Literature DB >> 17971728

Novel furanoid alpha-substitued alpha-amino acid as a potent turn mimic in peptide synthesis.

Miroslava Martinková1, Jozef Gonda, Jana Raschmanová.   

Abstract

A stereoselective approach has been developed to the new sugar amino acid and potential potent turn mimic 5-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-3-methoxycarbonylamino-alpha-D-xylofuranose 3-C-carboxylic acid (12), via the [3,3]-sigmatropic rearrangement of allylic thiocyanates (Z)-6 and (E)-7, prepared from D-xylose. The synthesis of a new dipeptide 13 is also described.

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Year:  2006        PMID： 17971728      PMCID： PMC6148663          DOI： 10.3390/11070564

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  8 in total

1.  Functionalized amino acid anticonvulsants: synthesis and pharmacological evaluation of conformationally restricted analogues.

Authors:  A LeTiran; J P Stables; H Kohn
Journal:  Bioorg Med Chem       Date:  2001-10       Impact factor: 3.641

2.  Methods for anomeric carbon-linked and fused sugar amino Acid synthesis: the gateway to artificial glycopeptides.

Authors:  A Dondoni; A Marra
Journal:  Chem Rev       Date:  2000-12-13       Impact factor: 60.622

Review 3.  Carbohydrate-based mimetics in drug design: sugar amino acids and carbohydrate scaffolds.

Authors:  Sibylle A W Gruner; Elsa Locardi; Elisabeth Lohof; Horst Kessler
Journal:  Chem Rev       Date:  2002-02       Impact factor: 60.622

4.  Development of co- and post-translational synthetic strategies to C-neoglycopeptides.

Authors:  Glenn J McGarvey; Tyler E Benedum; Frank W Schmidtmann
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

5.  Cyclic homooligomers from sugar amino acids: synthesis, conformational analysis, and significance.

Authors:  E Locardi; M Stöckle; S Gruner; H Kessler
Journal:  J Am Chem Soc       Date:  2001-08-29       Impact factor: 15.419

6.  Synthesis of a galacto-configured C-ketoside-based gamma-sugar-amino acid and its use in peptide coupling reactions.

Authors:  Frank Schweizer; Ole Hindsgaul
Journal:  Carbohydr Res       Date:  2006-04-17       Impact factor: 2.104

7.  Synthesis of new sugar amino acid derivatives of D-glucosamine.

Authors:  Juan Xie
Journal:  Carbohydr Res       Date:  2003-02-14       Impact factor: 2.104

Review 8.  Glycosamino acids: building blocks for combinatorial synthesis-implications for drug discovery.

Authors:  Frank Schweizer
Journal:  Angew Chem Int Ed Engl       Date:  2002-01-18       Impact factor: 15.336
  8 in total
  1 in total

1.  A novel synthetic approach to C-glycosyl-D- and L-alanines.

Authors:  Miroslava Martinková; Jozef Gonda; Jana Raschmanová; Alexandra Novodomská; Jozef Kozísek; Lucia Perasinová
Journal:  Molecules       Date:  2008-12-15       Impact factor: 4.411
  1 in total

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