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4 article(s) from Xu, Houchao

Functional characterisation of twelve terpene synthases from actinobacteria

Anuj K. Chhalodia,
Houchao Xu,
Georges B. Tabekoueng,
Binbin Gu,
Kizerbo A. Taizoumbe,
Lukas Lauterbach and
Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100

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Figure 1: Terpenes produced by characterised terpene synthases.

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Figure 2: Phylogenetic tree constructed from the amino acid sequences of 4018 terpene synthase homologs. Blue...

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Figure 3: A) Total ion chromatogram of the products obtained from FPP with KkdCS, B) EI mass spectrum of 10, ...

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Figure 4: Total ion chromatograms of the products obtained from FPP A) with SlADS and B) with SsADS, C) EI ma...

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Figure 5: Total ion chromatograms of the products obtained with NbEIZS A) from FPP and B) from GPP, and C) st...

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Figure 6: Total ion chromatogram of the products obtained with SfES. Peak numbers refer to compound numbers i...

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Scheme 1: A) Cope rearrangement of 24 and 26. B) Cyclisation mechanism from FPP to 23, identifying compound 26...

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Figure 7: Total ion chromatograms of the products obtained with A) SsHS, B) ScHS, C) SfHS, and D) SmGAS. Peak...

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Figure 8: A) Total ion chromatogram of the products obtained from GGPP with KkAS, B) EI mass spectrum of allo...

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Full Research Paper

Published 15 Sep 2023

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Germacrene B – a central intermediate in sesquiterpene biosynthesis

Houchao Xu and
Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

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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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Published 20 Feb 2023

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Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

Houchao Xu,
Anne Wochele,
Minghe Luo,
Gregor Schnakenburg,
Yuhui Sun,
Heike Brötz-Oesterhelt and
Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165, doi:10.3762/bjoc.18.120

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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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Letter

Published 07 Sep 2022

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The enzyme mechanism of patchoulol synthase

Houchao Xu,
Bernd Goldfuss,
Gregor Schnakenburg and
Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 13–24, doi:10.3762/bjoc.18.2

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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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Published 03 Jan 2022

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