Literature DB >> 20161157

Thio-mediated synthesis of derivatized N-linked glycopeptides using isonitrile chemistry.

Xiangyang Wu1, Yu Yuan, Xuechen Li, Samuel J Danishefsky.   

Abstract

The reaction of oligosaccharide isonitriles with peptide thioacids in the presence of bulky thiophenol as activator to provide N-linked glycopeptides at room temperature is described.

Entities:  

Year:  2009        PMID： 20161157      PMCID： PMC2735058          DOI： 10.1016/j.tetlet.2009.06.005

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  9 in total

1.  Synthesis of glycopeptides containing carbohydrate and Peptide recognition motifs.

Authors:  H Herzner; T Reipen; M Schultz; H Kunz
Journal:  Chem Rev       Date:  2000-12-13       Impact factor: 60.622

2.  Side reactions in peptide synthesis. II. Formation of succinimide derivatives from aspartyl residues.

Authors:  M Bodanszky; S Natarajan
Journal:  J Org Chem       Date:  1975-08-22       Impact factor: 4.354

3.  Thio-mediated two-component coupling reaction of carboxylic acids and isonitriles under mild conditions.

Authors:  Xiangyang Wu; Xuechen Li; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-04-08       Impact factor: 2.415

4.  Preparation and reactions of N-thioformyl peptides from amino thioacids and isonitriles.

Authors:  Yu Yuan; Jianglong Zhu; Xuechen Li; Xiangyang Wu; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-05-20       Impact factor: 2.415

5.  Addressing mechanistic issues in the coupling of isonitriles and carboxylic acids: potential routes to peptidic constructs.

Authors:  Xuechen Li; Yu Yuan; Cindy Kan; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-09-11       Impact factor: 15.419

6.  On the two-component microwave-mediated reaction of isonitriles with carboxylic acids: regarding alleged formimidate carboxylate mixed anhydrides.

Authors:  Xuechen Li; Yu Yuan; William F Berkowitz; Louis J Todaro; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-09-11       Impact factor: 15.419

7.  N-methylation of peptides: a new perspective in medicinal chemistry.

Authors:  Jayanta Chatterjee; Chaim Gilon; Amnon Hoffman; Horst Kessler
Journal:  Acc Chem Res       Date:  2008-07-18       Impact factor: 22.384

8.  New chemistry with old functional groups: on the reaction of isonitriles with carboxylic acids--a route to various amide types.

Authors:  Xuechen Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-03-28       Impact factor: 15.419

9.  Side reactions in peptide synthesis. VII. Sequence dependence in the formation of aminosuccinyl derivatives from beta-benzyl-aspartyl peptides.

Authors:  M Bodanszky; J Z Kwei
Journal:  Int J Pept Protein Res       Date:  1978-08
  9 in total
  5 in total

1.  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

Review 2.  A fascinating journey into history: exploration of the world of isonitriles en route to complex amides.

Authors:  Rebecca M Wilson; Jennifer L Stockdill; Xiangyang Wu; Xuechen Li; Paul A Vadola; Peter K Park; Ping Wang; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-24       Impact factor: 15.336

3.  Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.

Authors:  Ting Wang; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2013-07-02       Impact factor: 11.205

4.  On the synthesis of conformationally modified peptides through isonitrile chemistry: implications for dealing with polypeptide aggregation.

Authors:  Xiangyang Wu; Peter K Park; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

5.  A Simple Method for the Conversion of Carboxylic Acids into Thioacids with Lawesson's Reagent.

Authors:  Yu Rao; Xuechen Li; Pavel Nagorny; Joji Hayashida; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-12-02       Impact factor: 2.415
  5 in total

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