Literature DB >> 21846113

In situ carboxyl activation using a silatropic switch: a new approach to amide and peptide constructions.

Wenting Wu1, Zhihui Zhang, Lanny S Liebeskind.   

Abstract

The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1° and 2° amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.

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Year:  2011        PMID： 21846113      PMCID： PMC3189452          DOI： 10.1021/ja2065158

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  20 in total

1.  Mechanism of thio acid/azide amidation.

Authors:  Robert V Kolakowski; Ning Shangguan; Ronald R Sauers; Lawrence J Williams
Journal:  J Am Chem Soc       Date:  2006-05-03       Impact factor: 15.419

Review 2.  Emerging methods in amide- and peptide-bond formation.

Authors:  Jeffery W Bode
Journal:  Curr Opin Drug Discov Devel       Date:  2006-11

3.  Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature.

Authors:  Raed M Al-Zoubi; Olivier Marion; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Promising general solution to the problem of ligating peptides and glycopeptides.

Authors:  Ping Wang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-11-04       Impact factor: 15.419

5.  Oxidative acylation using thioacids.

Authors:  R Liu; L E Orgel
Journal:  Nature       Date:  1997-09-04       Impact factor: 49.962

6.  Total synthesis of cyclosporine: access to N-methylated peptides via isonitrile coupling reactions.

Authors:  Xiangyang Wu; Jennifer L Stockdill; Ping Wang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

7.  Thio acid/azide amidation: an improved route to N-acyl sulfonamides.

Authors:  Kristin N Barlett; Robert V Kolakowski; Sreenivas Katukojvala; Lawrence J Williams
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005

8.  Epimerization-free block synthesis of peptides from thioacids and amines with the Sanger and Mukaiyama reagents.

Authors:  David Crich; Indrajeet Sharma
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Amino acid and peptide synthesis and functionalization by the reaction of thioacids with 2,4-dinitrobenzenesulfonamides.

Authors:  David Crich; Kasinath Sana; Songpo Guo
Journal:  Org Lett       Date:  2007-09-27       Impact factor: 6.005

10.  The reaction of thio acids with azides: a new mechanism and new synthetic applications.

Authors:  Ning Shangguan; Sreenivas Katukojvala; Rachel Greenberg; Lawrence J Williams
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419
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  2 in total

1.  Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides.

Authors:  Andrew G Roberts; Eric V Johnston; Jae-Hung Shieh; Joseph P Sondey; Ronald C Hendrickson; Malcolm A S Moore; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2015-10-01       Impact factor: 15.419

2.  Solvent-Free Iron(III) Chloride-Catalyzed Direct Amidation of Esters.

Authors:  Blessing D Mkhonazi; Malibongwe Shandu; Ronewa Tshinavhe; Sandile B Simelane; Paseka T Moshapo
Journal:  Molecules       Date:  2020-02-26       Impact factor: 4.411
  2 in total

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