Literature DB >> 21539308

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

Xiangyang Wu1, Peter K Park, Samuel J Danishefsky.   

Abstract

A method for introducing a dimethyleneoxy constraint joining the N atoms of two consecutive amino acids in the context of a polypeptide has been developed. This constraint can profoundly affect the tendency of a polypeptide to suffer aggregation and desolubilization, and it can be readily removed under mild conditions.

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Year:  2011        PMID： 21539308      PMCID： PMC3108857          DOI： 10.1021/ja2023898

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


  26 in total

Review 1.  Chemical modifications designed to improve peptide stability: incorporation of non-natural amino acids, pseudo-peptide bonds, and cyclization.

Authors:  Luca Gentilucci; Rossella De Marco; Lucia Cerisoli
Journal:  Curr Pharm Des       Date:  2010       Impact factor: 3.116

2.  The 'O-acyl isopeptide method' for the synthesis of difficult sequence-containing peptides: application to the synthesis of Alzheimer's disease-related amyloid beta peptide (Abeta) 1-42.

Authors:  Youhei Sohma; Yoshio Hayashi; Maiko Kimura; Yousuke Chiyomori; Atsuhiko Taniguchi; Masato Sasaki; Tooru Kimura; Yoshiaki Kiso
Journal:  J Pept Sci       Date:  2005-07       Impact factor: 1.905

3.  Depsipeptide methodology for solid-phase peptide synthesis: circumventing side reactions and development of an automated technique via depsidipeptide units.

Authors:  Irene Coin; Rudolf Dölling; Eberhard Krause; Michael Bienert; Michael Beyermann; Calin Dan Sferdean; Louis A Carpino
Journal:  J Org Chem       Date:  2006-08-04       Impact factor: 4.354

Review 4.  The medicinal chemistry of peptides.

Authors:  J J Nestor
Journal:  Curr Med Chem       Date:  2009       Impact factor: 4.530

5.  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

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

Authors:  Xiangyang Wu; Yu Yuan; Xuechen Li; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-08-12       Impact factor: 2.415

Review 7.  Amyloid-beta as a "difficult sequence" in solid phase peptide synthesis.

Authors:  Anna K Tickler; Andrew B Clippingdale; John D Wade
Journal:  Protein Pept Lett       Date:  2004-08       Impact factor: 1.890

8.  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

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.  Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages.

Authors:  Xuechen Li; Samuel J Danishefsky
Journal:  Nat Protoc       Date:  2008       Impact factor: 13.491
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  2 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
  2 in total

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