Literature DB >> 20161291

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

Yu Yuan1, Jianglong Zhu, Xuechen Li, Xiangyang Wu, Samuel J Danishefsky.   

Abstract

The preparation of N-thioformyl peptides from amino thioacids and isonitriles at room temperature is described.

Entities:  

Year:  2009        PMID： 20161291      PMCID： PMC2690959          DOI： 10.1016/j.tetlet.2009.02.205

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


  4 in total

1.  Design and synthesis of novel bis(L-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity.

Authors:  Xiaozhong Fu; Saihong Jiang; Chuan Li; Jian Xin; Yushe Yang; Ruyun Ji
Journal:  Bioorg Med Chem Lett       Date:  2006-10-12       Impact factor: 2.823

2.  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

3.  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

4.  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
  4 in total
  15 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

2.  Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.

Authors:  Aaron M Dumas; Gary A Molander; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

3.  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

4.  Exploiting the Divalent Nature of Isonitriles: a novel Pictet-Spengler Amidination process.

Authors:  Federico Medda; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2014-05-01       Impact factor: 2.415

Review 5.  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

6.  Encouraging progress in the ω-aspartylation of complex oligosaccharides as a general route to β-N-linked glycopolypeptides.

Authors:  Ping Wang; Xuechen Li; Jianglong Zhu; Jin Chen; Yu Yuan; Xiangyang Wu; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2011-01-05       Impact factor: 15.419

7.  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

8.  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

9.  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

10.  Thio FCMA intermediates as strong acyl donors: a general solution to the formation of complex amide bonds.

Authors:  Yu Rao; Xuechen Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419
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