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      A route to diastereomerically pure phenylglycine thioester peptides: crucial intermediates for investigating glycopeptide antibiotic biosynthesis

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          Abstract

          Non-ribosomal peptides contain an array of amino acid building blocks that can present challenges for the synthesis of important intermediates. Here we report a route to incorporate phenylglycine residues in peptide thioesters without significant racemisation.

          Abstract

          Non-ribosomal peptides contain an array of amino acid building blocks that can present challenges for the synthesis of important intermediates. Here, we report the synthesis of glycopeptide antibiotic (GPA) thioester peptides that retains the crucial stereochemical purity of the terminal phenylglycine residue, which we show is essential for the enzymatic GPA cyclisation cascade.

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          Nonribosomal Peptide Synthesis-Principles and Prospects

          Roderich Süssmuth, Andi Mainz (2017)
          Article 0 comments Cited 217 times – based on 0 reviews     Review now
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            Chemical synthesis of proteins using peptide hydrazides as thioester surrogates.

            Ji-Shen Zheng, Shan-shan Tang, Yun-Kun Qi … (2013)
            This protocol provides a detailed procedure for the chemical synthesis of proteins through native chemical ligation of peptide hydrazides. The two crucial stages of this protocol are (i) the solid-phase synthesis of peptide hydrazides via Fmoc chemistry and (ii) the native chemical ligation of peptide hydrazides through in situ NaNO2 activation and thiolysis. This protocol may be of help in the synthesis of proteins that are not easily produced by recombinant technology and that include acid-sensitive modifications; it also does not involve the use of hazardous HF. The utility of the protocol is shown for the total synthesis of 140-aa-long α-synuclein, a protein that has an important role in the development of Parkinson's disease. The whole synthesis of the target protein α-synuclein in milligram scale takes ~30 working days.
            Article 0 comments Cited 73 times – based on 0 reviews     Review now
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              Glycopeptide antibiotic biosynthesis.

              Swathi Thaker, Kalinka Koteva, Grace Yim … (2013)
              Glycopeptides such as vancomycin, teicoplanin and telavancin are essential for treating infections caused by Gram-positive bacteria. Unfortunately, the dwindled pipeline of new antibiotics into the market and the emergence of glycopeptide-resistant enterococci and other resistant bacteria are increasingly making effective antibiotic treatment difficult. We have now learned a great deal about how bacteria produce antibiotics. This information can be exploited to develop the next generation of antimicrobials. The biosynthesis of glycopeptides via nonribosomal peptide assembly and unusual amino acid synthesis, crosslinking and tailoring enzymes gives rise to intricate chemical structures that target the bacterial cell wall. This review seeks to describe recent advances in our understanding of both biosynthesis and resistance of these important antibiotics.
              Article 0 comments Cited 55 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Journal ID (publisher-id): CHCOFS
                Title: Chemical Communications
                Abbreviated Title: Chem. Commun.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1359-7345
                ISSN (Electronic): 1364-548X
                Publication date Created: 2018
                Publication date (Electronic): 2018
                Volume: 54
                Issue: 17
                Pages: 2146-2149
                Affiliations
                [1 ]EMBL Australia, Monash University
                [2 ]Clayton
                [3 ]Australia
                [4 ]The Monash Biomedicine Discovery Institute
                [5 ]Department of Biochemistry and Molecular Biology and ARC Centre of Excellence in Advanced Molecular Imaging
                [6 ]Department of Biomolecular Mechanisms
                [7 ]Max Planck Institute for Medical Research
                [8 ]Jahnstrasse 29
                [9 ]Germany
                Article
                DOI: 10.1039/C7CC09409D
                SO-VID: a3133cb2-05b3-4a04-9db9-73aca430fc86
                Copyright © © 2018
                License:

                http://creativecommons.org/licenses/by/3.0/

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