Literature DB >> 21348452

Synthesis of thiazolidine thioester peptides and acceleration of native chemical ligation.

Julien Dheur1, Nathalie Ollivier, Oleg Melnyk.   

Abstract

Thiazolidine thioester peptides were synthesized by reacting bis(2-sulfanylethyl)amido peptides with glyoxylic acid at pH 1. A significant increase in Native Chemical Ligation (NCL) rate was observed with thiazolidine thioesters compared to 3-mercaptopropionic acid-thioester analogues. The method is of particular interest for accelerating valine-cysteine peptide bond formation.

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Year:  2011        PMID： 21348452     DOI： 10.1021/ol2002804

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


  8 in total

Review 1.  Expanding the chemical toolbox for the synthesis of large and uniquely modified proteins.

Authors:  Somasekhar Bondalapati; Muhammad Jbara; Ashraf Brik
Journal:  Nat Chem       Date:  2016-04-22       Impact factor: 24.427

2.  Direct Fmoc-chemistry-based solid-phase synthesis of peptidyl thioesters.

Authors:  Indrajeet Sharma; David Crich
Journal:  J Org Chem       Date:  2011-07-13       Impact factor: 4.354

3.  One-pot chemical synthesis of small ubiquitin-like modifier protein-peptide conjugates using bis(2-sulfanylethyl)amido peptide latent thioester surrogates.

Authors:  Emmanuelle Boll; Hervé Drobecq; Nathalie Ollivier; Annick Blanpain; Laurent Raibaut; Rémi Desmet; Jérôme Vicogne; Oleg Melnyk
Journal:  Nat Protoc       Date:  2015-01-15       Impact factor: 13.491

4.  Shifting Native Chemical Ligation into Reverse through N→S Acyl Transfer.

Authors:  Derek Macmillan; Anna Adams; Bhavesh Premdjee
Journal:  Isr J Chem       Date:  2011-10-05       Impact factor: 3.333

Review 5.  Chemical reactions directed Peptide self-assembly.

Authors:  Dnyaneshwar B Rasale; Apurba K Das
Journal:  Int J Mol Sci       Date:  2015-05-13       Impact factor: 5.923

6.  Accelerating chemoselective peptide bond formation using bis(2-selenylethyl)amido peptide selenoester surrogates.

Authors:  Laurent Raibaut; Marine Cargoët; Nathalie Ollivier; Yun Min Chang; Hervé Drobecq; Emmanuelle Boll; Rémi Desmet; Jean-Christophe M Monbaliu; Oleg Melnyk
Journal:  Chem Sci       Date:  2016-01-11       Impact factor: 9.825

7.  Single Posttranslational Modifications in the Central Repeat Domains of Tau4 Impact its Aggregation and Tubulin Binding.

Authors:  Doris Ellmer; Manuel Brehs; Mahmood Haj-Yahya; Hilal A Lashuel; Christian F W Becker
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-17       Impact factor: 15.336

8.  Accelerated microfluidic native chemical ligation at difficult amino acids toward cyclic peptides.

Authors:  Nathalie Ollivier; Thomas Toupy; Ruben C Hartkoorn; Rémi Desmet; Jean-Christophe M Monbaliu; Oleg Melnyk
Journal:  Nat Commun       Date:  2018-07-20       Impact factor: 14.919
  8 in total

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