Literature DB >> 19462032

A general strategy for the preparation of C-terminal peptide alpha-ketoacids by solid phase peptide synthesis.

Lei Ju1, Jeffrey W Bode.   

Abstract

A new cyanosulfur-ylide based linker makes possible the synthesis of C-terminal peptide alpha-ketoacids by solid phase synthesis. The preparation of the requisite linker and its application to a variety of C-terminal peptide alpha-ketoacids with unprotected side chains is reported.

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Year:  2009        PMID： 19462032      PMCID： PMC2907649          DOI： 10.1039/b901198f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  15 in total

Review 1.  Synthesis of native proteins by chemical ligation.

Authors:  P E Dawson; S B Kent
Journal:  Annu Rev Biochem       Date:  2000       Impact factor: 23.643

2.  A phosphorane as supported acylanion equivalent: linker reagents for smooth and versatile C-C coupling reactions.

Authors:  Steffen Weik; Jörg Rademann
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-06       Impact factor: 15.336

Review 3.  Evolving strategies for protein synthesis converge on native chemical ligation.

Authors:  Derek Macmillan
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

4.  C-acylations of polymeric phosphoranylidene acetates for C-terminal variation of peptide carboxylic acids.

Authors:  Adeeb El-Dahshan; Steffen Weik; Jörg Rademann
Journal:  Org Lett       Date:  2007-02-17       Impact factor: 6.005

5.  High-yielding Staudinger ligation of a phosphinothioester and azide to form a peptide.

Authors:  B L Nilsson; L L Kiessling; R T Raines
Journal:  Org Lett       Date:  2001-01-11       Impact factor: 6.005

6.  Iterative, aqueous synthesis of beta3-oligopeptides without coupling reagents.

Authors:  Nancy Carrillo; Eric A Davalos; Justin A Russak; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2006-02-08       Impact factor: 15.419

7.  Water-soluble phosphinothiols for traceless staudinger ligation and integration with expressed protein ligation.

Authors:  Annie Tam; Matthew B Soellner; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2007-08-22       Impact factor: 15.419

8.  Oxo-ester mediated native chemical ligation: concept and applications.

Authors:  Qian Wan; Jin Chen; Yu Yuan; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

9.  Stereoretentive synthesis and chemoselective amide-forming ligations of C-terminal peptide alpha-ketoacids.

Authors:  Lei Ju; Alexander R Lippert; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2008-03-12       Impact factor: 15.419

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

Authors:  David Crich; Kasinath Sana; Songpo Guo
Journal:  Org Lett       Date:  2007-09-27       Impact factor: 6.005
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  4 in total

1.  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

2.  Asymmetric synthesis of enantiopure isoxazolidinone monomers for the synthesis of β-oligopeptides by chemoselective amide ligation.

Authors:  M Elisa Juarez-Garcia; Shouyun Yu; Jeffrey W Bode
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

3.  Chemoselective protection of alpha-ketoacids by direct annulations with oximes.

Authors:  Melissa A Flores; Jeffrey W Bode
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

4.  Prevention of aspartimide formation during peptide synthesis using cyanosulfurylides as carboxylic acid-protecting groups.

Authors:  Kevin Neumann; Jakob Farnung; Simon Baldauf; Jeffrey W Bode
Journal:  Nat Commun       Date:  2020-02-20       Impact factor: 14.919
  4 in total

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