Chemistry, Biology, and Medicine of the Glycopeptide Antibiotics

doi:10.1002/(sici)1521-3773(19990802)38:15<2096::aid-anie2096>3.0.co;2-f

PMID: 10425471DOI: 10.1002/(sici)1521-3773(19990802)38:15<2096::aid-anie2096>3.0.co;2-fJul 30, 1999

Chemistry, Biology, and Medicine of the Glycopeptide Antibiotics

Angewandte Chemie

K C NicolaouN Winssinger

Abstract

The war against infectious bacteria is not over! Although vancomycin and glycopeptide antibiotics have provided a strong last line of defence against many drug-resistant bacteria, their overuse has given rise to more dangerous strains of bacteria. An understanding of the chemistry and biology of these highly complex glycopeptides are destined to play a crucial role in the discovery of new antibiotics.

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Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

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Evolution-guided discovery of antibiotics that inhibit peptidoglycan remodelling

Feb 14, 2020·Nature·Elizabeth J CulpGerard D Wright

Crystal structure of OxyC, a cytochrome P450 implicated in an oxidative C-C coupling reaction during vancomycin biosynthesis

Jul 31, 2003·The Journal of Biological Chemistry·Olena PylypenkoIlme Schlichting

The direct catalytic enantioselective synthesis of protected aryl beta-hydroxy-alpha-amino acids

Jan 29, 2005·Angewandte Chemie·Michael C WillisMatthew P John

Membrane Disruption and Enhanced Inhibition of Cell-Wall Biosynthesis: A Synergistic Approach to Tackle Vancomycin-Resistant Bacteria

Oct 17, 2015·Angewandte Chemie·Venkateswarlu YarlagaddaJayanta Haldar

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Mar 19, 2016·Chemistry, an Asian Journal·Meijia ChangYou Huang

Efficient synthesis of beta-hydroxy-alpha-amino acid derivatives via direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes

Jul 21, 2010·Chemistry : a European Journal·Xiaohong ChenXiaoming Feng

Glycopeptide Antibiotic Resistance Genes: Distribution and Function in the Producer Actinomycetes

Jul 14, 2020·Frontiers in Microbiology·Oleksandr YushchukFlavia Marinelli

Teicoplanin biosynthesis: unraveling the interplay of structural, regulatory, and resistance genes

Feb 21, 2020·Applied Microbiology and Biotechnology·Oleksandr YushchukVictor Fedorenko

Atropisomerism, biphenyls, and fluorine: a comparison of rotational barriers and twist angles

May 4, 2004·Chembiochem : a European Journal of Chemical Biology·Frédéric Leroux

Complex oxidation chemistry in the biosynthetic pathways to vancomycin/teicoplanin antibiotics

Jun 18, 2009·Chembiochem : a European Journal of Chemical Biology·Paul F Widboom, Steven D Bruner

Fibrous nano-silica (KCC-1)-supported palladium catalyst: Suzuki coupling reactions under sustainable conditions

Nov 17, 2011·ChemSusChem·Aziz FihriVivek Polshettiwar

Sequential In Vitro Cyclization by Cytochrome P450 Enzymes of Glycopeptide Antibiotic Precursors Bearing the X-Domain from Nonribosomal Peptide Biosynthesis

Nov 10, 2015·Angewandte Chemie·Clara BriekeMax J Cryle

Toward a global picture of bacterial secondary metabolism

Jan 27, 2019·Journal of Industrial Microbiology & Biotechnology·Mohammad R Seyedsayamdost

New Molecular Insights into the Inhibition of Dipeptidyl Peptidase-4 by Natural Cyclic Peptide Oxytocin

Oct 31, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Veera C S R ChittepuGuillermo Osorio-Revilla

Hexapeptide derivatives of glycopeptide antibiotics: tools for mechanism of action studies

Jul 18, 2002·Antimicrobial Agents and Chemotherapy·Norris E AllenRichard C Thompson

Strained cyclophane natural products: macrocyclization at its limits

Jun 26, 2012·Natural Product Reports·Tanja Gulder, Phil S Baran

Direct-type aldol reactions of fluorenylidene-protected/activated glycine esters with aldehydes for the synthesis of β-hydroxy-α-amino acid derivatives

Mar 31, 2012·Chemistry, an Asian Journal·Raphaël RahmaniShū Kobayashi

Alanine scan of the peptide antibiotic feglymycin: assessment of amino acid side chains contributing to antimicrobial activity

Mar 1, 2013·Chembiochem : a European Journal of Chemical Biology·Anne HänchenRoderich D. Süssmuth

Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates

Mar 5, 2015·Angewandte Chemie·Raquel de la CampaDarren J Dixon

A highly enantioselective four-component reaction for the efficient construction of chiral β-hydroxy-α-amino acid derivatives

Feb 26, 2013·Chemical Communications : Chem Comm·Yu QianWenhao Hu

Asymmetric Suzuki-Miyaura cross-coupling for the synthesis of chiral biaryl compounds as potential monophosphine ligands

Mar 3, 2015·Chemistry : a European Journal·Yan-Na Ma, Shang-Dong Yang

Interaction Mechanism between Antibiotics and Humic Acid by UV-Vis Spectrometry

Sep 5, 2018·International Journal of Environmental Research and Public Health·Xiaoyu YuanYaqian Zhao

Phylogenetic reconciliation reveals the natural history of glycopeptide antibiotic biosynthesis and resistance

Aug 14, 2019·Nature Microbiology·Nicholas WaglechnerGerard D Wright

Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst

Mar 19, 2019·Chemical Science·Siddhartha AkasapuMaciej A Walczak

The total synthesis of C-glycosides with completely resolved seven-carbon backbone polyol stereochemistry: stereochemical correlations and access to L-configured and other rare carbohydrates

Jan 5, 2002·Chemistry : a European Journal·H M HoffmannC B Stark

Vancomycin-induced morphological transformation of self-assembled amphiphilic diacetylene supramolecules

Jan 16, 2007·Chemical Communications : Chem Comm·Kun Ha ParkJong-Man Kim

Synthesis of biaryl compounds through three-component assembly: ambidentate effect of the tert-butyldimethylsilyl group for regioselective Diels-Alder and Hiyama coupling reactions

Sep 10, 2008·Angewandte Chemie·Shuji AkaiYasuyuki Kita

Remarkably effective phosphanes simply with a PPh2 moiety: application to Pd-catalysed cross-coupling reactions for tetra-ortho-substituted biaryl syntheses

Jun 22, 2010·Chemistry : a European Journal·Chau Ming SoFuk Yee Kwong

Synthesis of single-chain sugar arrays

Jan 25, 2013·Angewandte Chemie·Nathalie BaradelJean-François Lutz

2-carbomethoxy-3-hydroxyquinoxaline-di-N-oxide as a novel ligand for the copper-catalyzed coupling reaction of phenols and aryl halides

Jan 23, 2013·Organic & Biomolecular Chemistry·Yatao QiuSheng Jiang

Old and New Glycopeptide Antibiotics: Action and Resistance

Jan 1, 2014·Antibiotics·Elisa BindaGiorgia Letizia Marcone

CuI/Oxalamide Catalyzed Couplings of (Hetero)aryl Chlorides and Phenols for Diaryl Ether Formation

Apr 14, 2016·Angewandte Chemie·Mengyang FanDawei Ma

A review on cell wall synthesis inhibitors with an emphasis on glycopeptide antibiotics

Jan 26, 2017·MedChemComm·Paramita SarkarJayanta Haldar

Halogenation of glycopeptide antibiotics occurs at the amino acid level during non-ribosomal peptide synthesis

Oct 11, 2017·Chemical Science·Tiia KittiläEvi Stegmann

Genetic insights into the mechanism of teicoplanin self-resistance in Actinoplanes teichomyceticus

Jan 19, 2020·The Journal of Antibiotics·Oleksandr YushchukVictor Fedorenko

The Biosynthesis of Vancomycin-Type Glycopeptide Antibiotics-New Insights into the Cyclization Steps This work was supported by the Deutsche Forschungsgemeinschaft (SFB 323). We thank M. Schierle, Dr. S. Stevanovic and Prof. H.-G. Rammensee for help with Edman degradation and J. Turner, Prof. B. List and Prof. D. Boger (La Jolla, USA) for discussions on the work

May 16, 2001·Angewandte Chemie·Daniel BischoffRoderich D. Süssmuth

The Biosynthesis of Vancomycin-Type Glycopeptide Antibiotics-The Order of the Cyclization Steps This work was supported by the Deutsche Forschungsgemeinschaft (SFB 323) and by a grant of the EU (MEGATOP, QLK3-1999-00650). R. D. S. gratefully acknowledges the support of a Feodor-Lynen Fellowship granted by the Alexander-von-Humboldt Stiftung. We thank Corina Bihlmaier and Volker Pfeifer for help with transformation and Southern hybridization, J. A. Moss (La Jolla (USA)) for critical comments on the manuscrip

Oct 31, 2002·Angewandte Chemie·Daniel BischoffRoderich D. Süssmuth

Synthesis of 1,5-triazole bridged vancomycin CDE-ring bicyclic mimics using RuAAC macrocyclization

Apr 11, 2013·Chemical Communications : Chem Comm·Jinqiang ZhangRob M J Liskamp

Generation of New Complestatin Analogues by Heterologous Expression of the Complestatin Biosynthetic Gene Cluster from Streptomyces chartreusis AN1542

Jul 8, 2016·Chembiochem : a European Journal of Chemical Biology·Ok-Kyung ParkWon-Gon Kim

A genetics-free method for high-throughput discovery of cryptic microbial metabolites

Jan 9, 2019·Nature Chemical Biology·Fei XuMohammad R Seyedsayamdost

Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions

Dec 5, 2019·Angewandte Chemie·Mor Ben-LuluDoron Pappo

Nonomuraea sp. ATCC 55076 harbours the largest actinomycete chromosome to date and the kistamicin biosynthetic gene cluster

Jun 20, 2017·MedChemComm·Behnam NazariMohammad R Seyedsayamdost

Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance

Jun 30, 2012·Chemical Society Reviews·K C NicolaouHeraklidia A Ioannidou

GPAHex-A synthetic biology platform for Type IV-V glycopeptide antibiotic production and discovery

Oct 18, 2020·Nature Communications·Min XuGerard D Wright

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