Literature DB >> 11869108

Total synthesis of the cyclic heptapeptide Argyrin B: a new potent inhibitor of T-cell independent antibody formation.

Steven V Ley1, Alain Priour, Christoph Heusser.   

Abstract

[structure: see text] The total synthesis of Argyrin B (1) is presented using a synthetic plan that is convergent and flexible and conserves the stereogenic centers. The unusual amino acid 4-methoxy tryptophan (6) was obtained via an enzymatic resolution. Cyclization followed by oxidative elimination of the phenylseleno cysteine to the sensitive dehydroalanine afforded synthetic 1.

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Year:  2002        PMID: 11869108     DOI: 10.1021/ol017184m

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  On the substrate specificity of dehydration by lacticin 481 synthetase.

Authors:  Xingang Zhang; Wilfred A van der Donk
Journal:  J Am Chem Soc       Date:  2007-02-01       Impact factor: 15.419

2.  Total synthesis of the opioid agonistic indole alkaloid mitragynine and the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-Nb-methylgeissoschizol.

Authors:  Jun Ma; Wenyuan Yin; Hao Zhou; James M Cook
Journal:  Org Lett       Date:  2007-08-08       Impact factor: 6.005

3.  The cyclic octapeptide antibiotic argyrin B inhibits translation by trapping EF-G on the ribosome during translocation.

Authors:  Maximiliane Wieland; Mikael Holm; Emily J Rundlet; Martino Morici; Timm O Koller; Tinashe P Maviza; Domen Pogorevc; Ilya A Osterman; Rolf Müller; Scott C Blanchard; Daniel N Wilson
Journal:  Proc Natl Acad Sci U S A       Date:  2022-05-02       Impact factor: 12.779

4.  Gatorbulin-1, a distinct cyclodepsipeptide chemotype, targets a seventh tubulin pharmacological site.

Authors:  Susan Matthew; Qi-Yin Chen; Ranjala Ratnayake; Charles S Fermaintt; Daniel Lucena-Agell; Francesca Bonato; Andrea E Prota; Seok Ting Lim; Xiaomeng Wang; J Fernando Díaz; April L Risinger; Valerie J Paul; Maria Ángela Oliva; Hendrik Luesch
Journal:  Proc Natl Acad Sci U S A       Date:  2021-03-02       Impact factor: 11.205

5.  General approach to the total synthesis of 9-methoxy-substituted indole alkaloids: synthesis of mitragynine, as well as 9-methoxygeissoschizol and 9-methoxy-N(b)-methylgeissoschizol.

Authors:  Jun Ma; Wenyuan Yin; Hao Zhou; Xuebin Liao; James M Cook
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

6.  Identification of elongation factor G as the conserved cellular target of argyrin B.

Authors:  Beat Nyfeler; Dominic Hoepfner; Deborah Palestrant; Christina A Kirby; Lewis Whitehead; Robert Yu; Gejing Deng; Ruth E Caughlan; Angela L Woods; Adriana K Jones; S Whitney Barnes; John R Walker; Swann Gaulis; Ervan Hauy; Saskia M Brachmann; Philipp Krastel; Christian Studer; Ralph Riedl; David Estoppey; Thomas Aust; N Rao Movva; Zuncai Wang; Michael Salcius; Gregory A Michaud; Gregory McAllister; Leon O Murphy; John A Tallarico; Christopher J Wilson; Charles R Dean
Journal:  PLoS One       Date:  2012-09-10       Impact factor: 3.240

7.  Unlocking Reactivity of TrpB: A General Biocatalytic Platform for Synthesis of Tryptophan Analogues.

Authors:  David K Romney; Javier Murciano-Calles; Jöri E Wehrmüller; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2017-07-28       Impact factor: 15.419

8.  Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors.

Authors:  Grace E Hubbell; Jetze J Tepe
Journal:  RSC Chem Biol       Date:  2020-09-16

9.  Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation.

Authors:  Franziska Gille; Andreas Kirschning
Journal:  Beilstein J Org Chem       Date:  2016-03-22       Impact factor: 2.883

10.  Biotechnological production optimization of argyrins - a potent immunomodulatory natural product class.

Authors:  Domen Pogorevc; Rolf Müller
Journal:  Microb Biotechnol       Date:  2021-11-01       Impact factor: 5.813

  10 in total

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