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

Molecules. 2006 Jul 26;11(7):564-73. doi: 10.3390/11070564.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Dipeptides / chemical synthesis
  • Dipeptides / chemistry
  • Molecular Mimicry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Protein Conformation
  • Protein Structure, Secondary
  • Stereoisomerism
  • Sugar Acids / chemistry*

Substances

  • Amino Acids
  • Dipeptides
  • Peptides
  • Sugar Acids