Literature DB >> 26251952

Amide and Peptide Bond Formation in Water at Room Temperature.

Christopher M Gabriel1, Megan Keener1, Fabrice Gallou2, Bruce H Lipshutz1.   

Abstract

A general and environmentally responsible method for the formation of amide/peptide bonds in an aqueous micellar medium is described. Use of uronium salt (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU) as a coupling reagent, 2,6-lutidine, and TPGS-750-M represents mild conditions associated with these valuable types of couplings. The aqueous reaction medium is recyclable leading to low E Factors.

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Year:  2015        PMID： 26251952     DOI： 10.1021/acs.orglett.5b01812

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


  7 in total

Review 1.  Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives.

Authors:  Andrew Jordan; Callum G J Hall; Lee R Thorp; Helen F Sneddon
Journal:  Chem Rev       Date:  2022-02-24       Impact factor: 72.087

2.  Designer Micelles Accelerate Flux Through Engineered Metabolism in E. coli and Support Biocompatible Chemistry.

Authors:  Stephen Wallace; Emily P Balskus
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-08       Impact factor: 15.336

3.  Fabrication and evaluation of a γ-PGA-based self-assembly transferrin receptor-targeting anticancer drug carrier.

Authors:  Li Zhang; Xiaoyu Zhu; Shijia Wu; Yazhou Chen; Shiming Tan; Yingjie Liu; Wenzheng Jiang; Jing Huang
Journal:  Int J Nanomedicine       Date:  2018-11-22

Review 4.  Catalytic and non-catalytic amidation of carboxylic acid substrates.

Authors:  Keyvan Pedrood; Saeed Bahadorikhalili; Vahid Lotfi; Bagher Larijani; Mohammad Mahdavi
Journal:  Mol Divers       Date:  2021-06-13       Impact factor: 2.943

5.  Highly efficient on-DNA amide couplings promoted by micelle forming surfactants for the synthesis of DNA encoded libraries.

Authors:  James H Hunter; Matthew J Anderson; Isaline F S F Castan; Jessica S Graham; Catherine L A Salvini; Harriet A Stanway-Gordon; James J Crawford; Andrew Madin; Garry Pairaudeau; Michael J Waring
Journal:  Chem Sci       Date:  2021-06-22       Impact factor: 9.825

6.  Atom-economic catalytic amide synthesis from amines and carboxylic acids activated in situ with acetylenes.

Authors:  Thilo Krause; Sabrina Baader; Benjamin Erb; Lukas J Gooßen
Journal:  Nat Commun       Date:  2016-06-10       Impact factor: 14.919

7.  Promiscuous activity of C-acyltransferase from Pseudomonas protegens: synthesis of acetanilides in aqueous buffer.

Authors:  Anna Żądło-Dobrowolska; Nina G Schmidt; Wolfgang Kroutil
Journal:  Chem Commun (Camb)       Date:  2018-03-29       Impact factor: 6.222
  7 in total

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