Literature DB >> 19697932

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

Yu Rao1, Xuechen Li, Samuel J Danishefsky.   

Abstract

Novel methodology for the formation of amide bonds under neutral conditions is described. Evidence is presented that the active acyl donors are thio FCMA intermediates, generated from the reactions of thioacids with isonitriles.

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Year:  2009        PMID： 19697932      PMCID： PMC2756580          DOI： 10.1021/ja906005j

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


  20 in total

Review 1.  Emerging methods in amide- and peptide-bond formation.

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

2.  Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

Authors:  Per Restorp; Julius Rebek
Journal:  J Am Chem Soc       Date:  2008-08-13       Impact factor: 15.419

3.  On the Preparation of Enantiomerically Pure Isonitriles from Amino Acid Esters and Peptides.

Authors:  Jianglong Zhu; Xiangyang Wu; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-02-04       Impact factor: 2.415

4.  Coupling reactions of hindered isonitriles and hindered alkyl thioacids: Mechanistic studies.

Authors:  Jennifer L Stockdill; Xiangyang Wu; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-09-09       Impact factor: 2.415

5.  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

6.  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

7.  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

Review 8.  Combined approaches to the synthesis and study of glycoproteins.

Authors:  Gonçalo J L Bernardes; Bastien Castagner; Peter H Seeberger
Journal:  ACS Chem Biol       Date:  2009-09-18       Impact factor: 5.100

9.  The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms.

Authors:  Gavin O Jones; Xuechen Li; Amy E Hayden; K N Houk; Samuel J Danishefsky
Journal:  Org Lett       Date:  2008-08-16       Impact factor: 6.005

10.  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
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  22 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.  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.  Total Chemical Synthesis and Folding of All-l and All-d Variants of Oncogenic KRas(G12V).

Authors:  Adam M Levinson; John H McGee; Andrew G Roberts; Gardner S Creech; Ting Wang; Michael T Peterson; Ronald C Hendrickson; Gregory L Verdine; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2017-05-22       Impact factor: 15.419

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.  Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide 18O-labeling.

Authors:  Jessica P Shackleford; Bo Shen; Jeffrey N Johnston
Journal:  Proc Natl Acad Sci U S A       Date:  2011-12-19       Impact factor: 11.205

8.  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 9.  Rethinking amide bond synthesis.

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

10.  Revisiting oxytocin through the medium of isonitriles.

Authors:  Ting Wang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-08-02       Impact factor: 15.419
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