34 article(s) from Dickschat, Jeroen S
- Review
- Published 20 Feb 2023
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Scheme 1: Possible cyclisation modes of FPP.
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Scheme 2: Structures of germacrene B (1), germacrene A (2) and hedycaryol (3).
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Scheme 3: The chemistry of germacrene B (1). A) Synthesis from germacrone (4), B) the four conformers of 1 es...
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Scheme 4: The chemistry of germacrene B (1). A) Cyclisation of 1 to 9 and 10 upon treatment with alumina, B) ...
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Scheme 5: Possible cyclisation reactions upon reprotonation of 1. A) Cyclisations to eudesmane sesquiterpenes...
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Scheme 6: Cyclisation modes for 1 to the eudesmane skeleton. A) The reprotonation of 1 at C-1 potentially lea...
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Scheme 7: The sesquiterpenes derived from cation I1. WMR = Wagner–Meerwein rearrangement.
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Scheme 8: The sesquiterpenes derived from cation I1. A) Pyrolysis of 23 to yield 9 and 10, B) deprotonation–r...
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Scheme 9: The sesquiterpenes derived from cation I1. A) Acid-catalysed conversion of 18 into 26, B) conversio...
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Scheme 10: The sesquiterpenes derived from cation I1. A) Formation of 20 by pyrolysis of 33, B) acid-catalysed...
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Scheme 11: The sesquiterpenes derived from cation I2. WMR = Wagner–Meerwein rearrangement.
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Scheme 12: The sesquiterpenes derived from cation I2. A) Acid catalysed conversion of 41 into 38, B) dehydrati...
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Scheme 13: The sesquiterpenes derived from cation I3. WMR = Wagner–Meerwein rearrangement.
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Scheme 14: Cyclisation modes for 1 to the guaiane skeleton. A) The reprotonation of 1 at C-4 potentially leads...
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Scheme 15: The sesquiterpenes derived from cations K1, K2 and K4. A) Mechanisms of formation for compounds 53–...
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Scheme 16: The sesquiterpenes derived from cations L1–L4. A) Mechanisms of formation for compounds 54, 56, 59 ...
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- Letter
- Published 07 Sep 2022
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Scheme 1: Structures of hangtaimycin (1) and its co-metabolites.
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Scheme 2: First synthetic route towards TDD (4).
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Figure 1: HPLC analyses of (Z)-4 on a chiral stationary phase. A) Nearly racemic 4 from the first synthetic r...
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Scheme 3: Second synthetic route towards TDD ((Z)-4).
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Figure 2: X-ray structure of (rac)-4.
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Figure 3: Bioactivity testing with hangtaimycin (1). A) Growth retardation of model species B. subtilis 168 a...
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Supp. Info
- Letter
- Published 08 Jul 2022
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Scheme 1: Biosynthesis of 2-MIB (1). A) Naturally observed pathway through methylation of GPP to 2-Me-GPP by ...
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Figure 1: A) Active site of 2MIBS with the bound substrate surrogate 2FGPP (generated with Pymol from the cry...
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Scheme 2: Synthesis of (R)- and (S)-2-Me-LPP.
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Figure 2: Structures of 2MIBS side products and spontaneous degradation products of 2-Me-LPP. The enantiomers...
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Figure 3: Total ion chromatograms of extracts from an incubation of A) enantiomerically pure (R)-2-Me-LPP wit...
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Scheme 3: Hypothetical mechanism for the isomerization of (S)-2-Me-LPP through 2-Me-GPP to (R)-2-Me-LPP.
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- Published 03 Jan 2022
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Figure 1: Initially assigned structures for patchoulol by Treibs (1) and by Büchi (2). Structures of patchoul...
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Scheme 1: Biosynthesis of patchoulol (part I). A) Cyclisation mechanism from FPP to 3 as suggested by Croteau...
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Scheme 2: Biosynthesis of patchoulol (part II). A) Cyclisation mechanism from FPP to 3 as suggested by Akhila...
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Scheme 3: Biosynthesis of patchoulol (part III). A) Cyclisation mechanism from FPP to 3 as suggested by Faral...
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Figure 2: ORTEP representation of patchoulol (3). Cu Kα, Flack parameter: −0.1(2); P2(true) = 1.000, P3(false...
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Scheme 4: Determination of the absolute configurations of compounds 3 and 12 through stereoselective labellin...
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Scheme 5: Labelling experiments on the biosynthesis of patchoulol (3, part 1). Black dots indicate 13C-labell...
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Scheme 6: Labelling experiments on the biosynthesis of patchoulol (3, part 2). Black dots indicate 13C-labell...
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Figure 3: Energy profile from DFT calculations (Gibbs energies at 298 K, mPW1PW91/6-311 + G(d,p)//B97D3/6-31G...
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Figure 4: Structure elucidation of (2S,3S,7S,10R)-guaia-1,11-dien-10-ol (17) and structure of its known stere...
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- Letter
- Published 17 Sep 2021
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Figure 1: Highly conserved residues in the active site of SdS for Mg2+ complexation, substrate recognition an...
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Figure 2: The products of SmTS1. A) Structures of sestermobaraenes A–F (1–6) and sestermobaraol (7). B) The t...
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Figure 3: Swiss homology modelling of SmTS1. A) Superimposition of the SdS crystal structure (green) with the...
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Figure 4: Products and relative activities of SmTS1 and its variants. Bars left of the dashed line show relat...
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Figure 5: Total ion chromatogram of an extract from an incubation of GGPP with the SmTS1 A222V variant.
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Figure 6: Relative activities of SmTS1 and its variants towards GFPP (blue bars) and GGPP (yellow bars), and ...
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Scheme 1: Determination of the enantiomeric composition of 8 and 9 obtained from GGPP with SmTS1 enzyme varia...
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Figure 7: Determination of the absolute configuration of compounds 8 and 9. Partial HSQC spectra of A) unlabe...
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- Published 26 Feb 2021
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Scheme 1: Volatile allyl sulfides. A) Compounds known from garlic oil, B) mechanism of formation from alliin (...
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Scheme 2: Degradation of DMSP by marine bacteria. A) Hydrolysis or lysis to DMS, B) demethylation pathway lea...
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Scheme 3: Synthesis of DMSP derivatives.
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Figure 1: Sulfur volatiles released by agar plate cultures of marine bacteria fed with DAllSP or AllMSP.
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Figure 2: Total ion chromatograms of CLSA extracts obtained from feeding experiments with DAllSP fed to A) P....
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Scheme 4: Proposed mechanisms for the formation of sulfur volatiles from DAllSP and AllMSP.
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Figure 3: EI mass spectrum and fragmentation pattern of the unknown volatiles A) methyl 3-(allyldisulfanyl)pr...
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Scheme 5: Synthesis of A) methyl 3-(allyldisulfanyl)propanoate (26) and B) methyl 3-(methylsulfonyl)propanoat...
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Figure 4: Total ion chromatograms of CLSA extracts obtained from the feeding experiments with AllMSP fed to A...
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- Published 11 Feb 2021
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Scheme 1: Sulfur metabolism in bacteria from the roseobacter group. A) DMSP demethylation by DmdABCD, B) DMSP...
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Figure 1: Total ion chromatograms of headspace extracts from A) C. marinus DSM 100036T, B) C. neptunius DSM 2...
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Figure 2: Structures of the identified volatile compounds in the headspace extracts from six Celeribacter typ...
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Figure 3: EI mass spectra of A) unlabeled 2-(methyldisulfanyl)benzothiazole (41) and of labeled 41 after feed...
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Scheme 2: Synthesis of sulfur-containing compounds detected in the Celeribacter headspace extracts. A) Synthe...
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Supp. Info
- Letter
- Published 19 Nov 2020
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Figure 1: The structures of the bacterial sesterterpenes sestermobaraenes A–F (1–6) and sestermobaraol (7) fr...
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Figure 2: Position-specific mass shift analyses for 1. Carbons that contribute fully to the formation of a fr...
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Scheme 1: The EIMS fragmentation mechanisms for 1 explaining the formation of the fragment ions at m/z = 325,...
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Scheme 2: The EIMS fragmentation mechanisms for 1 explaining the formation of fragment ions at m/z = 206 and ...
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Figure 3: Position-specific mass shift analyses for 2. The carbons that contribute fully to the formation of ...
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Scheme 3: The EIMS fragmentation mechanisms for 2 explaining the formation of the fragment ions at m/z = 325,...
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Scheme 4: The EIMS fragmentation mechanisms for 2 explaining the formation of the fragment ions at m/z = 203 ...
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Figure 4: The position-specific mass shift analyses for 3. Carbons that contribute fully to the formation of ...
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Scheme 5: The EIMS fragmentation mechanisms for 3 explaining the formation of the fragment ions at m/z = 325,...
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Scheme 6: The EIMS fragmentation mechanisms for 3 explaining the formation of the fragment ion at m/z = 206 a...
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- Published 29 May 2019
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Figure 1: Whole-genome phylogenetic analyses of Streptomyces species. Rooted maximum likelihood phylogeny of ...
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Figure 2: Structures of the products of the ten most abundant terpene synthases in Streptomyces.
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Scheme 1: Mechanism for the cyclisation of FPP to geosmin.
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Scheme 2: Biosynthesis of 2-MIB (2). First, GPP is methylated to 14 by a SAM-dependent methyltransferase, fol...
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Scheme 3: Oxidation products derived from 3 by the cytochrome P450 monooxygenase that is genetically clustere...
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Scheme 4: Biosynthesis of cyclooctatin (20) from 7.
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Figure 3: Phylogenetic tree of geosmin synthases. Unrooted maximum likelihood phylogenetic tree of 92 geosmin...
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Figure 4: Phylogenetic tree of 2-MIB synthases. Unrooted maximum likelihood phylogenetic tree of 48 2-MIB syn...
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Figure 5: Phylogenetic tree of epi-isozizaene synthases. Unrooted maximum likelihood phylogenetic tree of 42 ...
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- Published 02 May 2019
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Figure 1: Total ion chromatograms of hexane extracts from the incubations of HcS with A) FPP, B) GPP and C) G...
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Figure 2: Structures of HcS products arising A) from FPP together with related oxidation product 9, B) from G...
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Scheme 1: Initial steps of the cyclisation of GPP towards monoterpene products [34]. Both pathways are likely co-...
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Scheme 2: Late stage cyclisations of the himachalyl cation B to HcS products 1–6. Alternative mechanistic and...
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Figure 3: EI mass spectrum of 1 arising from an incubation of (2-2H)GPP and IPP with FPPS and HcS showing a l...
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Figure 4: Stereochemical course of the final deprotonation step towards 3, 5 and 6 investigated by GC–MS. EI ...
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Scheme 3: Proposed cyclisation mechanism towards cation B via an initial 1,11-cyclisation (path A) and an hyp...
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Figure 5: Total ion chromatogram of hexane extracts from HcS incubations with A) (R)-NPP, B) (S)-NPP and C) (...
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Figure 6: The origin of the two diastereotopic methyl groups in 1. Partial 13C NMR spectrum of A) unlabelled 1...
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Figure 7: Stereochemical course of the 1,11-cyclisation at C-1 for 7. Partial HSQC spectra of HcS incubation ...
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Figure 8: Investigation of the 1,3-hydride shift in the cyclisation towards 1. Partial 13C NMR spectra of A) ...
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Figure 9: Stereochemical course of the 1,3-hydride shift at C-10 in 1. Partial HSQC spectra of A) unlabelled 1...
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Figure 10: Position specific mass shift analysis for selected EIMS ions of HcS products. Black dots represent ...
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Supp. Info
- Letter
- Published 27 Mar 2019
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Figure 1: Structures of achiral terpenes: (E)-β-farnesene (1), α-humulene (2), 1,8-cineol (3) and sodorifen (4...
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Figure 2: A) Total ion chromatogram of a hexane extract from the incubation of FPP with BbS and B) EI mass sp...
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Scheme 1: Cyclisation mechanism to 5 involving either the intermediates (R)-NPP and (S)-A (path A) or (S)-NPP...
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Figure 3: Total ion chromatograms of hexane extracts from incubation experiments with BbS and A) (R)-NPP, B) (...
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Figure 4: Hypothetical BbS active site comparable conformational folds of A) FPP, B) (R)- and C) (S)-NPP expl...
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- Published 04 Dec 2018
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Figure 1: Structures of fungal volatiles. Trichodiene (1), aristolochene (2), (R)-oct-1-en-3-ol (3), 3,4-dime...
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Figure 2: Total ion chromatogram of a CLSA headspace extract from Hypoxylon griseobrunneum MUCL 53754. Peak n...
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Figure 3: Volatiles from Hypoxylon griseobrunneum.
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Figure 4: EI mass spectra of A) 2,4,5-trimethylanisole (24), B) the coeluting mixture of 3,4-dimethylanisole (...
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Scheme 1: Synthesis of trimethylanisoles 24 and 24d.
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Scheme 2: Hypothetical biosynthesis of 24. ACP: acyl carrier protein, AT: acyl transferase, KR: ketoreductase...
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Figure 5: Biosynthesis of 24. Feeding of (methyl-2H3)methionine resulted in the incorporation of labelling in...
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Scheme 3: Hypothetical biosynthesis of 25 and 26.
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Figure 6: Total ion chromatogram of a CLSA headspace extract from Hypoxylon macrocarpum STMA 130423. Peak num...
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Figure 7: Volatiles from Hypoxylon macrocarpum.
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Figure 8: EI mass spectra of A) 3,4-dimethoxybenzaldehyde (42), B) 3,4,5-trimethoxytoluene (44), and C) 2,4,5...
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Scheme 4: Synthesis of 2,3,4-trimethoxytoluene (44a).
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- Published 05 Jun 2018
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Scheme 1: Biosynthesis of AHLs by ACP-dependent LuxI type enzymes.
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Figure 1: Total ion chromatograms of the FAME extracts of A) P. inhibens 2.10, B) P. inhibens DSM17395, C) P....
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Scheme 2: Synthesis of N-pantothenoylcysteamine thioesters (PCEs) for feeding experiments with AHL synthases.
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Figure 2: Total ion chromatograms of the extracts from competition experiments using recombinant PgaI2 from P...
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- Published 24 Apr 2018
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Figure 1: Total ion chromatograms of headspace extracts from A) Aspergillus fischeri NRRL 181, B) Aspergillus...
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Scheme 1: Volatiles from Aspergillus fischeri. For all chiral compounds in Schemes 1–5 the relative configura...
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Scheme 2: Biosynthesis of bisabolanes and related terpenes in A. fischeri.
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Scheme 3: Biosynthesis of daucanes in A. fischeri.
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Scheme 4: Volatiles from A. kawachii. A) Proposed biosynthesis of sesquiterpenes, B) other identified volatil...
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Scheme 5: Volatiles from A. clavatus.
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- Published 29 Mar 2018
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Figure 1: Structures of the widespread fungal volatiles oct-1-en-3-ol (1) and 6-pentyl-2H-pyran-2-one (2), th...
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Figure 2: Total-ion chromatogram of the bouquet from Hypoxylon invadens MUCL 54175 obtained by the CLSA heads...
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Figure 3: Identified volatile organic compounds from Hypoxylon invadens MUCL 54175.
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Figure 4: Mass spectra of volatiles from Hypoxylon invadens MUCL 54175. Mass spectra of A) 2,5-dimethylphenol...
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Scheme 1: Proposed common biosynthetic pathway to volatile aromatic compounds from Hypoxylon invadens.
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Scheme 2: Synthesis of 5-hydroxy-2-methyl-4H-chromen-4-one (19).
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- Published 12 Jan 2018
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Scheme 1: A selection of widespread fungal volatiles.
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Figure 1: Total ion chromatogram of a representative headspace extract from Daldinia clavata MUCL 47436. Peak...
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Scheme 2: Identified volatiles from Daldinia clavata MUCL 47436.
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Figure 2: Mass spectra of volatiles from D. clavata that were identified by synthesis.
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Scheme 3: Synthesis of manicone (10).
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Scheme 4: Synthesis of a racemic mixture of all four diastereomers of 11.
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Figure 3: Gas chromatographic analysis of 11 on a homochiral stationary phase. a) Synthetic mixture of all ei...
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Scheme 5: Enantioselective synthesis of (4R,5S,6S)-11c and (4S,5R,6S)-11d.
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Scheme 6: Epimerisations of (4R,5S,6S)-11c and (4S,5R,6S)-11d under basic conditions.
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Figure 4: Gas chromatographic analysis of 11 on a homochiral stationary phase. a) Synthetic mixture of all ei...
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Scheme 7: Proposed biosynthesis for (4R,5R,6S)-11a.
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Figure 5: Mass spectra of a) 6-methyl-5,6-dihydro-2H-pyran-2-one (9), b) 6-propyl-5,6-dihydro-2H-pyran-2-one,...
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Scheme 8: Synthesis of 6-methyl-5,6-dihydro-2H-pyran-2-one (9) and 6-nonyl-2H-pyran-2-one (17).
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- Published 23 Aug 2017
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Scheme 1: Germacrene A (1) and its Cope rearrangement to β-elemene (2).
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Figure 1: In vitro terpene synthase activity of the investigated recombinant enzyme from C. pinensis, showing...
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Scheme 2: Product obtained from the diterpene synthase from C. pinensis. (A) Structure of (1R,3E,7E,11S,12S)-...
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Figure 2: Determination of the absolute configuration of 3. (A) Partial HSQC spectrum of unlabelled 3 showing...
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Figure 3: Determination of the absolute configuration of 3. (A) Partial HSQC spectrum of unlabelled 3 showing...
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Figure 4: Assignment of H6α and H6β of 3. (A) Partial HSQC spectrum of unlabelled 3 showing the region for C6...
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Figure 5: Partial 13C NMR spectra of A) unlabeled 3, B) (13C1)-3 arising from incubation of HdS and GGPPS wit...
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Figure 6: Transient expression of 18-hydroxydolabella-3,7-diene synthase (HdS) in Nicotiana benthamiana. Tota...
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- Published 04 Nov 2016
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Figure 1: Selection of achiral terpenes.
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Scheme 1: Cyclisation of GPP to 1 via the (R)-terpinyl cation ((R)-6, left) or the (S)-terpinyl cation ((S)-6...
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Figure 2: Partial HSQC spectra showing the region of crosspeaks for HA and HB connected to C-3 and C-5 of A) ...
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Figure 3: A) Partial HSQC spectrum showing the region of crosspeaks of C-2 with its directly connected hydrog...
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Scheme 2: Mechanism for the cyclisation of FPP to corvol ethers A (19) and B (18). WMR: Wagner-Meerwein rearr...
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- Published 15 Aug 2016
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Figure 1: Structures of sesquiterpenes obtained by incubation of FPP with bacterial sesquiterpene cyclases.
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Figure 2: Contiguous spin systems observed by 1H,1H-COSY (bold), key HMBC and NOE correlations for a) α-amorp...
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Figure 3: Contiguous spin systems observed by 1H,1H-COSY (bold), key HMBC and NOE correlations for a) 7-epi-α...
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Scheme 1: Biosynthetic pathway from FPP to 7-epi-α-eudesmol (4).
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Figure 4: Incubation experiments with (6-13C)FPP and the 7-epi-α-eudesmol synthase in deuterium oxide. a) 13C...
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Figure 5: Incubation experiments with (13-13C)FPP. 13C NMR spectra of a) unlabelled 1 and (13-13C)-1, b) unla...
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- Published 05 Jul 2016
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Scheme 1: Structures of corvol ethers A (1) and B (2), epi-cubebol (3), and isodauc-8-en-11-ol (4). Carbon nu...
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Figure 1: Mass spectra of unlabelled 1 and all fifteen positional isomers of (13C1)-1.
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Scheme 2: PMAs and EIMS fragmentation mechanisms for the fragment ions A) m/z = 179, B) m/z = 161, C) m/z = 1...
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Figure 2: Mass spectra of unlabelled 2 and all fifteen positional isomers of (13C1)-2.
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Scheme 3: PMAs and EIMS fragmentation mechanisms for the fragment ions A) m/z = 179, B) m/z = 161, C) m/z = 1...
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Figure 3: Mass spectra of unlabelled 3 and all fifteen positional isomers of (13C1)-3.
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Scheme 4: PMAs and EIMS fragmentation mechanisms for the fragment ions A) m/z = 207, B) m/z = 179, C) m/z = 1...
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Figure 4: Mass spectra of unlabelled 4 and all fifteen positional isomers of (13C1)-4.
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Scheme 5: PMAs and EIMS fragmentation mechanisms for the fragment ions A) m/z = 207, B) m/z = 189, C) m/z = 1...
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- Review
- Published 09 Dec 2015
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Figure 1: Structures of lovastatin (1), aflatoxin B1 (2) and amphotericin B (3).
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Scheme 1: a) Structure of rhizoxin (4). b) Two possible mechanisms of chain branching catalysed by a branchin...
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Scheme 2: Structure of coelimycin P1 (8) and proposed biosynthetic formation from the putative PKS produced a...
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Scheme 3: Structure of trioxacarcin A (9) with highlighted carbon origins of the polyketide core from acetate...
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Scheme 4: Proposed biosynthetic assembly of clostrubin A (12). Bold bonds show intact acetate units.
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Figure 2: Structure of forazoline A (13).
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Figure 3: Structures of tyrocidine A (14) and teixobactin (15).
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Figure 4: Top: Structure of the NRPS product kollosin A (16) with the sequence N-formyl-D-Leu-L-Ala-D-Leu-L-V...
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Scheme 5: Proposed biosynthesis of aspirochlorine (20) via 18 and 19.
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Scheme 6: Two different macrocyclization mechanisms in the biosynthesis of pyrrocidine A (24).
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Figure 5: Structure of thiomarinol A (27). Bold bonds indicate carbon atoms derived from 4-hydroxybutyrate.
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Figure 6: Structures of artemisinin (28), ingenol (29) and paclitaxel (30).
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Figure 7: The revised (31) and the previously suggested (32) structure of hypodoratoxide and the structure of...
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Figure 8: Structure of the two interconvertible conformers of (1(10)E,4E)-germacradien-6-ol (34) studied with...
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Scheme 7: Proposed cyclization mechanism of corvol ethers A (42) and B (43) with the investigated reprotonati...
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Scheme 8: Predicted (top) and observed (bottom) 13C-labeling pattern in cyclooctatin (45) after feeding of [U-...
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Scheme 9: Proposed mechanism of the cyclooctat-9-en-7-ol (52) biosynthesis catalysed by CotB2. Annotated hydr...
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Scheme 10: Cyclization mechanism of sesterfisherol (59). Bold lines indicate acetate units; black circles repr...
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Scheme 11: Cyclization mechanisms to pentalenene (65) and protoillud-6-ene (67).
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Scheme 12: Reactions of chorismate catalyzed by three different enzyme subfamilies. Oxygen atoms originating f...
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Scheme 13: Incorporation of sulfur into tropodithietic acid (72) via cysteine.
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Scheme 14: Biosynthetic proposal for the starter unit of antimycin biosynthesis. The hydrogens at positions R1...
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- Letter
- Published 06 Aug 2014
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Figure 1: TDA and related natural products from Phaeobacter inhibens.
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Scheme 1: Synthesis of tropone-2-carboxylic acid (13).
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Scheme 2: Synthesis of halogenated TDA analogues.
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Scheme 3: Further compounds included in this SAR study.
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Figure 1: Alkaloids produced by Streptomyces strain FORM5.
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Figure 2: Part of the total ion chromatogram of the headspace extract of Streptomyces sp. FORM5 with the stru...
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Figure 3: Mass spectra of a) (E)-2-(pent-3-en-1-yl)pyridine (streptopyridine E, 8), b) (1Z,3E)-penta-1,3-dien...
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Scheme 1: Synthesis of streptopyridines A to E (8–12) and the 2-alkylpyridines 6 and 7.
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Figure 4: Total ion chromatograms of the product mixtures of isomers 9–12 synthesized under E-selective (a) a...
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Figure 5: Structures of piperidine derivatives 20–26.
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Figure 6: a) Mass spectrum of streptopyridine A (12), b) mass spectrum of 12 after feeding of 2 mM 13C2-sodiu...
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Scheme 2: Proposed biosynthesis of the streptopyridines. PKS: polyketide synthase; red: reduction; ta: transa...
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Figure 7: Compounds detected in the headspace of Streptomyces sp. FORM5.
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Figure 1: Terpenoids from Streptomyces griseus.
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Figure 2: Total ion chromatograms of CLSA headspace extracts from S. griseus obtained after (A) incubation on...
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Figure 3: Mass spectra of 1-epi-cubenol. (A) Mass spectrum of natural 3 obtained after growth on 65.GYM; (B) ...
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Figure 4: Ion chromatograms of fully deuterated 3 for (A) the molecular ion (m/z = 248, 247, and 246), and (B...
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Figure 1: Total ion chromatogram of a CLSA headspace extract from Geniculosporium.
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Figure 2: Mass spectra of A) the chlorinated volatile X and B) the chlorinated volatile Y.
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Figure 3: Constitutional isomers of chlorodimethoxybenzene as candidate structures for X.
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Scheme 1: Synthesis of chlorodimethoxybenzenes as reference compounds for X.
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Figure 4: Constitutional isomers of dichlorodimethoxybenzene as candidate structures for Y.
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Scheme 2: Synthesis of chlorodimethoxybenzenes as reference compounds for Y.
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Figure 5: Known natural products that are structurally related to 4b and 10b from Geniculosporium.
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Figure 6: Total ion chromatograms of headspace extracts from S. chartreusis. A) Growth on 84 GYM showing prod...
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Figure 7: Calicheamicin, a known iodinated compound from the actinomycete Micromonspora echinospora.
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Figure 1: Roseobacter clade metabolites.
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Scheme 1: Degradation of DMSP via (A) demethylation pathway and (B) cleavage pathways. FH4: tetrahydrofolate.
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Scheme 2: Sulfate reduction pathway and incorporation of sulfur into the amino acid pool. PAP: adenosine 3’,5...
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Figure 2: Volatiles from P. gallaeciensis DSM 17395 and R. pomeroyi DSS-3. Feeding of [2H6]DMSP results in de...
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Figure 3: Chromatograms of headspace extracts from P. gallaeciensis DSM 17395 after feeding of DMTeP by the u...
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Figure 4: Chromatograms of headspace extracts obtained after feeding of [2H6]DMSP by the use of SPME from (A) ...
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Figure 5: Chromatograms of headspace extracts from (A) R. pomeroyi DSS-3 wild type, (B) R. pomeroyi DSS-3 dmdA...
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Scheme 3: Synthesis of 34S-labeled thiosulfate and sulfate.
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Figure 6: Volatiles from P. gallaeciensis after feeding of selenate and selenite.
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Figure 7: Chromatograms of headspace extracts from P. gallaeciensis grown on (A) 50% MB2216, (B) 50% MB2216 +...
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Figure 8: Additional sulfur volatiles.
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Figure 1: Important metabolites in the interaction of bacteria from the Roseobacter clade with marine algae.
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Figure 2: (A) Total ion chromatogram of a headspace extract from R. pomeroyi, (B) structures of lactones rele...
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Figure 3: Mass spectra of the compounds 7–11 emitted by R. pomeroyi.
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Scheme 1: Synthesis of compounds 7–11. For these target structures the relative configurations are shown.
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Scheme 2: Enantioselective synthesis of (2R,4S)-7 and (2S,4S)-8.
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Figure 4: Enantioselective GC analyses for the assignment of the enantiomeric compositions of natural (2S,4R)-...
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Scheme 1: Fatty acid biosynthesis.
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Figure 1: Volatile methyl esters from bacteria.
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Figure 2: Compounds found in the headspace extracts of M. aurantiaca.
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Figure 3: Total ion chromatograms of the headspace extract from M. aurantiaca (A), and expansions of the tota...
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Figure 4: FAMEs identified in the headspace extracts from M. aurantiaca.
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Figure 5: Mass spectra of (A) methyl dodecanoate (83), (B) methyl 2-methyldodecanoate (10), (C) methyl 4-meth...
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Scheme 2: McLafferty fragmentation of FAMEs.
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Figure 6: The functional group increment FG(n)FAME, HP-5 MS.
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Scheme 3: Synthesis of FAMEs identified from M. aurantiaca.
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Scheme 4: Synthesis of the γ- and (ω−3)-methyl branched FAME 114.
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Figure 7: Mass spectra of tentatively identified methyl 4,8-dimethyldodecanoate (115) and methyl 8-ethyl-4-me...
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