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4 article(s) from Ducho, Christian

Oligonucleotide analogues with cationic backbone linkages

Melissa Meng and
Christian Ducho

Beilstein J. Org. Chem. 2018, 14, 1293–1308, doi:10.3762/bjoc.14.111

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Figure 1: Biological action of single-stranded oligonucleotides (ON): antigene and antisense pathways.

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Figure 2: Selected examples 1–6 of nucleic acid modifications based on additionally attached positively charg...

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Figure 3: Oligonucleotide analogues with artificial cationic backbone linkages discussed in this review: amin...

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Scheme 1: Structure of Letsinger's modified deoxyadenosyl dinucleotide 11 and synthesis of cationic oligonucl...

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Figure 4: Artificial cationic backbone linkages 19 and 20 which are structurally related to aminoalkylated ph...

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Scheme 2: Bruice's synthesis of guanidinium-linked DNG oligomer 29 in the 5'→3' direction (Troc = 2,2,2-trich...

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Scheme 3: Bruice's synthesis of purine-containing guanidinium-linked DNG oligomer 36 in the 3'→5' direction (...

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Scheme 4: Bruice's synthesis of S-methylthiourea-linked DNmt oligomer 43.

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Figure 5: Structure of the natural product muraymycin A1 (44) and design concept of nucleosyl amino acid (NAA...

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Scheme 5: Retrosynthetic summary of Ducho's synthesis of partially zwitterionic NAA-modified oligonucleotides ...

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Scheme 6: Retrosynthetic summary of Ducho's and Grossmann's synthesis of fully cationic NAA-modified oligonuc...

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Review

Published 04 Jun 2018

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Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

Daniel Wiegmann,
Stefan Koppermann,
Marius Wirth,
Giuliana Niro,
Kristin Leyerer and
Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

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Figure 1: Structures of the naturally occurring muraymycins isolated by McDonald et al. [22].

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Figure 2: Structures of selected classes of nucleoside antibiotics. Similarities to the muraymycins are highl...

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Figure 3: Structure of peptidoglycan. Long chains of glycosides (alternating GlcNAc (green) and MurNAc (blue)...

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Figure 4: Schematic representation of bacterial cell wall biosynthesis.

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Figure 5: Translocase I (MraY) catalyses the reaction of UDP-MurNAc-pentapeptide with undecaprenyl phosphate ...

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Figure 6: Proposed mechanisms for the MraY-catalysed reaction. A: Two-step mechanism postulated by Heydanek e...

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Scheme 1: First synthetic access towards simplified muraymycin analogues as reported by Yamashita et al. [76].

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Scheme 2: Synthesis of (+)-caprazol (19) reported by Ichikawa, Matsuda et al. [92].

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Scheme 3: Synthesis of the epicapreomycidine-containing urea dipeptide via C–H activation [96,97].

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Scheme 4: Synthesis of muraymycin D2 and its epimer reported by Ichikawa, Matsuda et al. [96,97].

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Scheme 5: Synthesis of the urea tripeptide unit as a building block for muraymycins reported by Kurosu et al. ...

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Scheme 6: Synthesis of the uridine-derived core structure of naturally occuring muraymycins reported by Ducho...

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Scheme 7: Synthesis of the epicapreomycidine-containing urea dipeptide from Garner's aldehyde reported by Duc...

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Scheme 8: Synthesis of a hydroxyleucine-derived aldehyde building block reported by Ducho et al. [107].

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Scheme 9: Synthesis of 5'-deoxy muraymycin C4 (65) as a closely related natural product analogue [78,109,110].

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Figure 7: Summary of modifications on semisynthetic muraymycin analogues tested by Lin et al. [86]. Most active c...

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Figure 8: Bioactive muraymycin analogues identified by Yamashita et al. [76].

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Figure 9: Muraymycin D2 and several non-natural lipidated analogues 91a–d [77,114].

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Figure 10: Non-natural muraymycin analogues with varying peptide structures [77,114].

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Figure 11: SAR results for several structural variations of the muraymycin scaffold.

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Figure 12: Muraymycin analogues designed for potential anti-Pseudomonas activity (most active analogues are hi...

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Scheme 10: Proposed outline pathway for muraymycin biosynthesis based on the analysis of the biosynthetic gene...

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Scheme 11: Biosynthesis of the nucleoside core structure of A-90289 antibiotics (which is identical to the mur...

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Scheme 12: Transaldolase-catalysed formation of the key intermediate GlyU 101 in the biosynthesis of muraymyci...

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Review

Published 22 Apr 2016

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NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A–T phosphoramidite building blocks

Boris Schmidtgall,
Claudia Höbartner and
Christian Ducho

Beilstein J. Org. Chem. 2015, 11, 50–60, doi:10.3762/bjoc.11.8

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Figure 1: Design concept of nucleosyl amino acid (NAA)-modified oligonucleotides 5 formally derived from stru...

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Scheme 1: Retrosynthetic analysis of target phosphoramidites (S)-7 and (R)-7 (BOM = benzyloxymethyl).

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Scheme 2: Synthesis of N-Fmoc-protected thymidine-derived nucleosyl amino acids (S)-9 and (R)-9; details on t...

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Scheme 3: Synthesis of protected 3'-amino-2',3'-dideoxyadenosine 8.

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Scheme 4: Synthesis of target phosphoramidites (S)-7 and (R)-7 and of two NAA-modified DNA oligonucleotides 30...

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Published 13 Jan 2015

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Amino acid motifs in natural products: synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

Oliver Ries,
Martin Büschleb,
Markus Granitzka,
Dietmar Stalke and
Christian Ducho

Beilstein J. Org. Chem. 2014, 10, 1135–1142, doi:10.3762/bjoc.10.113

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Figure 1: Structures of muraymycins A1, B6, C1 and D1 1a–d.

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Scheme 1: Synthesis of stereoisomerically pure amino alcohol 5 [32] and of derivative 6 suitable for X-ray crysta...

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Figure 2: Molecular structure of levulinyl ester 6. Anisotropic displacement parameters are depicted at the 5...

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Scheme 2: Synthesis of (2S,3S)-3-hydroxyleucine building blocks 13a,b useful for N-derivatization and of the ...

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Scheme 3: Synthesis of (2S,3S)-3-hydroxyleucine building block 19 useful for C-derivatization and of aldehyde ...

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Scheme 4: Synthesis of O-acylated (2S,3S)-3-hydroxyleucine derivatives 27 and 28.

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Scheme 5: Synthesis of 6-methylheptanoic acid (26).

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Scheme 6: Synthesis of Fmoc-protected building blocks 38 and 41 suitable for SPPS, with late-stage side chain...

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Published 16 May 2014

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