Literature DB >> 17900128

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

David Crich1, Kasinath Sana, Songpo Guo.   

Abstract

Readily prepared amino thioacids react at room temperature in DMF in the presence of cesium carbonate with 2,4-dinitrobenzenesulfonamides to give amides. When the sulfonamide is derived from an amino acid the method results in peptide bond formation, whereas the use of carbohydrate derived sulfonamides gives neoglycoconjugates.

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Year:  2007        PMID： 17900128     DOI： 10.1021/ol701583t

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


  19 in total

1.  Facile amide formation via S-nitrosothioacids.

Authors:  Jia Pan; Nelmi O Devarie-Baez; Ming Xian
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

2.  Expanding the limits of isonitrile-mediated amidations: on the remarkable stereosubtleties of macrolactam formation from synthetic seco-cyclosporins.

Authors:  Xiangyang Wu; Jennifer L Stockdill; Peter K Park; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

3.  AMIDE FORMATION BY DECARBOXYLATIVE CONDENSATION OF HYDROXYLAMINES AND α-KETOACIDS: N-[(1S)-1 PHENYLETHYL]-BENZENEACETAMIDE.

Authors:  Lei Ju; Jeffrey W Bode; Tatsuya Toma; Tohru Fukuyama
Journal:  Organic Synth       Date:  2010-12-01

4.  Mixed-phase synthesis of glycopeptides using a N-peptidyl-2,4-dinitrobenzenesulfonamide-thioacid ligation strategy.

Authors:  Partha Karmakar; Rommel S Talan; Steven J Sucheck
Journal:  Org Lett       Date:  2011-09-14       Impact factor: 6.005

5.  Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A Convenient Synthon for the Preparation of Substituted 1,4-Thiazepin-5-ones and Piperidinones via the Intermediacy of Thioacids.

Authors:  David Crich; Md Yeajur Rahaman
Journal:  Tetrahedron       Date:  2010-08-14       Impact factor: 2.457

Review 6.  Rethinking amide bond synthesis.

Authors:  Vijaya R Pattabiraman; Jeffrey W Bode
Journal:  Nature       Date:  2011-12-21       Impact factor: 49.962

7.  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

8.  Ring-opening of aziridine-2-carboxamides with carbohydrate C1-O-nucleophiles. Stereoselective preparation of alpha- and beta-O-glycosyl serine conjugates.

Authors:  Daniel A Ryan; David Y Gin
Journal:  J Am Chem Soc       Date:  2008-10-25       Impact factor: 15.419

9.  Reaction of thioacids with isocyanates and isothiocyanates: a convenient amide ligation process.

Authors:  David Crich; Kaname Sasaki
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

10.  Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides.

Authors:  Vishwanath Gaitonde; Steven J Sucheck
Journal:  J Carbohydr Chem       Date:  2012-07-02       Impact factor: 1.667
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