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1 article(s) from Koppermann, Stefan

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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Graphical Abstract

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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