Literature DB >> 18651745

Solid-phase synthesis of a cyclodepsipeptide: cotransin.

Irene Coin1, Monika Beerbaum, Peter Schmieder, Michael Bienert, Michael Beyermann.   

Abstract

The first solid-phase synthesis of cotransin--a cyclic depsipeptide having high pharmacological potential--was achieved, by a proper choice of coupling reagents and use of either TBAF or DBU for Fmoc removal to suppress the otherwise dominating, sequence-derived diketopiperazine formation. Starting the assembly from C-terminal lactic acid allowed fast and epimerization-free cyclization in solution. Novel conditions for orthogonal use of the Fmoc/Bsmoc-protection system were discovered, and an unexpected nucleophilic behavior of DBU was observed.

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Year:  2008        PMID： 18651745     DOI： 10.1021/ol800855p

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


  11 in total

1.  Comparative Flavivirus-Host Protein Interaction Mapping Reveals Mechanisms of Dengue and Zika Virus Pathogenesis.

Authors:  Priya S Shah; Nichole Link; Gwendolyn M Jang; Phillip P Sharp; Tongtong Zhu; Danielle L Swaney; Jeffrey R Johnson; John Von Dollen; Holly R Ramage; Laura Satkamp; Billy Newton; Ruth Hüttenhain; Marine J Petit; Tierney Baum; Amanda Everitt; Orly Laufman; Michel Tassetto; Michael Shales; Erica Stevenson; Gabriel N Iglesias; Leila Shokat; Shashank Tripathi; Vinod Balasubramaniam; Laurence G Webb; Sebastian Aguirre; A Jeremy Willsey; Adolfo Garcia-Sastre; Katherine S Pollard; Sara Cherry; Andrea V Gamarnik; Ivan Marazzi; Jack Taunton; Ana Fernandez-Sesma; Hugo J Bellen; Raul Andino; Nevan J Krogan
Journal:  Cell       Date:  2018-12-13       Impact factor: 41.582

2.  Macrolactonization of peptide thioesters catalyzed by imidazole and its application in the synthesis of kahalalide B and analogues.

Authors:  Yangmei Li; Marc Giulionatti; Richard A Houghten
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

3.  Inhibition of biosynthesis of human endothelin B receptor by the cyclodepsipeptide cotransin.

Authors:  Carolin Westendorf; Antje Schmidt; Irene Coin; Jens Furkert; Ingrid Ridelis; Dimitris Zampatis; Claudia Rutz; Burkhard Wiesner; Walter Rosenthal; Michael Beyermann; Ralf Schülein
Journal:  J Biol Chem       Date:  2011-07-30       Impact factor: 5.157

4.  Expanding the genetic code of Caenorhabditis elegans using bacterial aminoacyl-tRNA synthetase/tRNA pairs.

Authors:  Angela R Parrish; Xingyu She; Zheng Xiang; Irene Coin; Zhouxin Shen; Steven P Briggs; Andrew Dillin; Lei Wang
Journal:  ACS Chem Biol       Date:  2012-05-11       Impact factor: 5.100

5.  Total synthesis and structure-activity relationship studies of a series of selective G protein inhibitors.

Authors:  Xiao-Feng Xiong; Hang Zhang; Christina R Underwood; Kasper Harpsøe; Thomas J Gardella; Mie F Wöldike; Michael Mannstadt; David E Gloriam; Hans Bräuner-Osborne; Kristian Strømgaard
Journal:  Nat Chem       Date:  2016-07-25       Impact factor: 24.427

Review 6.  Marine Cyclic Peptides: Antimicrobial Activity and Synthetic Strategies.

Authors:  Ricardo Ribeiro; Eugénia Pinto; Carla Fernandes; Emília Sousa
Journal:  Mar Drugs       Date:  2022-06-15       Impact factor: 6.085

Review 7.  Natural products as modulators of eukaryotic protein secretion.

Authors:  Hendrik Luesch; Ville O Paavilainen
Journal:  Nat Prod Rep       Date:  2020-02-18       Impact factor: 13.423

8.  Synthesis of complex head-to-side-chain cyclodepsipeptides.

Authors:  Marta Pelay-Gimeno; Fernando Albericio; Judit Tulla-Puche
Journal:  Nat Protoc       Date:  2016-09-15       Impact factor: 13.491

9.  Defining a conformational consensus motif in cotransin-sensitive signal sequences: a proteomic and site-directed mutagenesis study.

Authors:  Wolfgang Klein; Carolin Westendorf; Antje Schmidt; Mercè Conill-Cortés; Claudia Rutz; Marcus Blohs; Michael Beyermann; Jonas Protze; Gerd Krause; Eberhard Krause; Ralf Schülein
Journal:  PLoS One       Date:  2015-03-25       Impact factor: 3.240

10.  Anthelmintic PF1022A: stepwise solid-phase synthesis of a cyclodepsipeptide containing N-methyl amino acids.

Authors:  Sebastian Lüttenberg; Frank Sondermann; Jürgen Scherkenbeck
Journal:  Tetrahedron       Date:  2011-12-16       Impact factor: 2.457
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