Literature DB >> 29423498

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

Julien Tailhades1, Melanie Schoppet, Anja Greule, Madeleine Peschke, Clara Brieke, Max J Cryle.   

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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Year:  2018        PMID： 29423498     DOI： 10.1039/c7cc09409d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 in total

Review 1.  Biological, chemical, and biochemical strategies for modifying glycopeptide antibiotics.

Authors:  Edward Marschall; Max J Cryle; Julien Tailhades
Journal:  J Biol Chem       Date:  2019-10-31       Impact factor: 5.157

Review 2.  Complex Regulatory Networks Governing Production of the Glycopeptide A40926.

Authors:  Rosa Alduina; Margherita Sosio; Stefano Donadio
Journal:  Antibiotics (Basel)       Date:  2018-04-05

3.  The biosynthetic implications of late-stage condensation domain selectivity during glycopeptide antibiotic biosynthesis.

Authors:  Melanie Schoppet; Madeleine Peschke; Anja Kirchberg; Vincent Wiebach; Roderich D Süssmuth; Evi Stegmann; Max J Cryle
Journal:  Chem Sci       Date:  2018-10-10       Impact factor: 9.825

4.  A proof-reading mechanism for non-proteinogenic amino acid incorporation into glycopeptide antibiotics.

Authors:  Milda Kaniusaite; Julien Tailhades; Edward A Marschall; Robert J A Goode; Ralf B Schittenhelm; Max J Cryle
Journal:  Chem Sci       Date:  2019-08-29       Impact factor: 9.825

5.  The Diiron Monooxygenase CmlA from Chloramphenicol Biosynthesis Allows Reconstitution of β-Hydroxylation during Glycopeptide Antibiotic Biosynthesis.

Authors:  Milda Kaniusaite; Robert J A Goode; Ralf B Schittenhelm; Thomas M Makris; Max J Cryle
Journal:  ACS Chem Biol       Date:  2019-12-10       Impact factor: 5.100

6.  Structures of a non-ribosomal peptide synthetase condensation domain suggest the basis of substrate selectivity.

Authors:  Thierry Izoré; Y T Candace Ho; Joe A Kaczmarski; Athina Gavriilidou; Ka Ho Chow; David L Steer; Robert J A Goode; Ralf B Schittenhelm; Julien Tailhades; Manuela Tosin; Gregory L Challis; Elizabeth H Krenske; Nadine Ziemert; Colin J Jackson; Max J Cryle
Journal:  Nat Commun       Date:  2021-05-04       Impact factor: 14.919

7.  The Cytochrome P450 OxyA from the Kistamicin Biosynthesis Cyclization Cascade is Highly Sensitive to Oxidative Damage.

Authors:  Anja Greule; Thierry Izoré; Daniel Machell; Mathias H Hansen; Melanie Schoppet; James J De Voss; Louise K Charkoudian; Ralf B Schittenhelm; Jeffrey R Harmer; Max J Cryle
Journal:  Front Chem       Date:  2022-04-08       Impact factor: 5.545

8.  Exploring modular reengineering strategies to redesign the teicoplanin non-ribosomal peptide synthetase.

Authors:  Milda Kaniusaite; Robert J A Goode; Julien Tailhades; Ralf B Schittenhelm; Max J Cryle
Journal:  Chem Sci       Date:  2020-08-24       Impact factor: 9.825
  8 in total

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