Literature DB >> 20161312

Synthesis of an enantiopure isoxazolidine monomer for β-aspartic acid in chemoselective β-oligopeptide synthesis.

Hiroshi Ishida1, Nancy Carrillo, Jeffrey W Bode.   

Abstract

The synthesis of an enantiopure isoxazolidine monomer for the incorporation of β(3)-apartic acid residues into β(3)-oligopeptides via chemoselective α-ketoacid-hydroxylamine amide formation. This route involves nitrone cycloaddition of 3-thiophenylpropanal and circumvents limitations of other potential starting materials.

Entities:  

Year:  2009        PMID： 20161312      PMCID： PMC2699312          DOI： 10.1016/j.tetlet.2009.02.045

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


  10 in total

Review 1.  beta-Peptides: from structure to function.

Authors:  R P Cheng; S H Gellman; W F DeGrado
Journal:  Chem Rev       Date:  2001-10       Impact factor: 60.622

2.  Enantioselective total syntheses of ditryptophenaline and ent-WIN 64821.

Authors:  L E Overman; D V Paone
Journal:  J Am Chem Soc       Date:  2001-09-26       Impact factor: 15.419

3.  Dynamic combinatorial libraries of disulfide cages in water.

Authors:  Kevin R West; Kyle D Bake; Sijbren Otto
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

Review 4.  Foldamers as versatile frameworks for the design and evolution of function.

Authors:  Catherine M Goodman; Sungwook Choi; Scott Shandler; William F DeGrado
Journal:  Nat Chem Biol       Date:  2007-05       Impact factor: 15.040

5.  Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and alpha-ketoacids.

Authors:  Jeffrey W Bode; Ryan M Fox; Kyle D Baucom
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-13       Impact factor: 15.336

Review 6.  The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.

Authors:  Dieter Seebach; Albert K Beck; Daniel J Bierbaum
Journal:  Chem Biodivers       Date:  2004-08       Impact factor: 2.408

7.  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

8.  Toward beta-amino acid proteins: design, synthesis, and characterization of a fifteen kilodalton beta-peptide tetramer.

Authors:  E James Petersson; Alanna Schepartz
Journal:  J Am Chem Soc       Date:  2008-01-01       Impact factor: 15.419

9.  Total synthesis of scytophycin C. 1. Stereoselective syntheses of the C(1)-C(18) segment and the C(19)-C(31) segment.

Authors:  Ryoichi Nakamura; Keiji Tanino; Masaaki Miyashita
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

10.  Lactol-directed osmylation. Stereodivergent synthesis of four C-19,20 apoptolidin diols from a single allylic hemiacetal.

Authors:  Youngsoon Kim; Philip L Fuchs
Journal:  Org Lett       Date:  2007-06-01       Impact factor: 6.005
  10 in total

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