Literature DB >> 21812451

Enzymatic timing and tailoring of macrolactamization in syringolin biosynthesis.

William M Wuest1, Daniel Krahn, Markus Kaiser, Christopher T Walsh.   

Abstract

The enzymatic activation of 3,4-dehydrolysine and subsequent formation of the 12-membered syringolin macrolactam were investigated. The timing of the desaturation was elucidated through the analysis of the initial adenylation domain of SylD. The SylD-TTE didomain was characterized and demonstrated to be the catalyst for formation of 12-membered macrocycles. When the SylD thioesterase domain was reacted with a family of acyclic CoA both natural and unnatural macrocycles were generated.

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Year:  2011        PMID： 21812451      PMCID： PMC3163001          DOI： 10.1021/ol2016687

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


  18 in total

1.  Total synthesis of syringolin A.

Authors:  Chunhui Dai; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

2.  Synthetic and structural studies on syringolin A and B reveal critical determinants of selectivity and potency of proteasome inhibition.

Authors:  Jérôme Clerc; Michael Groll; Damir J Illich; André S Bachmann; Robert Huber; Barbara Schellenberg; Robert Dudler; Markus Kaiser
Journal:  Proc Natl Acad Sci U S A       Date:  2009-04-09       Impact factor: 11.205

3.  Syrbactin class proteasome inhibitor-induced apoptosis and autophagy occurs in association with p53 accumulation and Akt/PKB activation in neuroblastoma.

Authors:  Crystal R Archer; Dana-Lynn T Koomoa; Erin M Mitsunaga; Jérôme Clerc; Mariko Shimizu; Markus Kaiser; Barbara Schellenberg; Robert Dudler; André S Bachmann
Journal:  Biochem Pharmacol       Date:  2010-04-01       Impact factor: 5.858

4.  Crystal structure of the surfactin synthetase-activating enzyme sfp: a prototype of the 4'-phosphopantetheinyl transferase superfamily.

Authors:  K Reuter; M R Mofid; M A Marahiel; R Ficner
Journal:  EMBO J       Date:  1999-12-01       Impact factor: 11.598

5.  Total synthesis of syringolin A and B.

Authors:  Michael C Pirrung; Goutam Biswas; Tannya R Ibarra-Rivera
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

6.  The natural product hybrid of Syringolin A and Glidobactin A synergizes proteasome inhibition potency with subsite selectivity.

Authors:  Jérôme Clerc; Nan Li; Daniel Krahn; Michael Groll; André S Bachmann; Bogdan I Florea; Herman S Overkleeft; Markus Kaiser
Journal:  Chem Commun (Camb)       Date:  2010-09-07       Impact factor: 6.222

7.  SylC catalyzes ureido-bond formation during biosynthesis of the proteasome inhibitor syringolin A.

Authors:  Heidi J Imker; Christopher T Walsh; William M Wuest
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419

8.  A plant pathogen virulence factor inhibits the eukaryotic proteasome by a novel mechanism.

Authors:  Michael Groll; Barbara Schellenberg; André S Bachmann; Crystal R Archer; Robert Huber; Tracy K Powell; Steven Lindow; Markus Kaiser; Robert Dudler
Journal:  Nature       Date:  2008-04-10       Impact factor: 49.962

9.  Functional analysis of genes involved in the synthesis of syringolin A by Pseudomonas syringae pv. syringae B301 D-R.

Authors:  Hans Amrein; Stefan Makart; José Granado; Roshani Shakya; Jana Schneider-Pokorny; Robert Dudler
Journal:  Mol Plant Microbe Interact       Date:  2004-01       Impact factor: 4.171

10.  Biosynthesis of the proteasome inhibitor syringolin A: the ureido group joining two amino acids originates from bicarbonate.

Authors:  Christina Ramel; Micha Tobler; Martin Meyer; Laurent Bigler; Marc-Olivier Ebert; Barbara Schellenberg; Robert Dudler
Journal:  BMC Biochem       Date:  2009-10-28       Impact factor: 4.059
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  2 in total

1.  Production of proteasome inhibitor syringolin A by the endophyte Rhizobium sp. strain AP16.

Authors:  Alexey Dudnik; Laurent Bigler; Robert Dudler
Journal:  Appl Environ Microbiol       Date:  2014-04-11       Impact factor: 4.792

2.  An accurate strategy for pointing the key biocatalytic sites of bre2691A protein for modification of the brevilaterin from Brevibacillus laterosporus.

Authors:  Panpan Han; Zhou Chen; Yangliu Liu; Aijin Ma; Siting Li; Yingmin Jia
Journal:  Microb Cell Fact       Date:  2022-09-19       Impact factor: 6.352
  2 in total

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