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

Org Lett. 2007 Mar 15;9(6):949-52. doi: 10.1021/ol062754+. Epub 2007 Feb 17.

Abstract

C-Acylations of polymer-supported 2-phosphoranylidene acetates ("linker reagents") with protected amino acids yielded 2-acyl-2-phosphoranylidene acetates as flexible intermediates for the C-terminal variation of carboxylic acids: peptidyl-2,3-diketoesters, peptidyl vinyl ketones, peptidyl-2-ketoaldehydes, and 1,3-diamino-2-hydroxy-propanes were obtained as products. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Acylation
  • Aldehydes / chemistry
  • Carboxylic Acids / chemistry*
  • Combinatorial Chemistry Techniques
  • Cross-Linking Reagents / chemistry
  • Diamines / chemistry
  • Esters / chemistry
  • Models, Chemical
  • Peptides / chemical synthesis*
  • Phosphoranes / chemistry*
  • Polymers / chemistry*
  • Resins, Synthetic / chemistry
  • Vinyl Compounds / chemistry

Substances

  • Acetates
  • Aldehydes
  • Carboxylic Acids
  • Cross-Linking Reagents
  • Diamines
  • Esters
  • Peptides
  • Phosphoranes
  • Polymers
  • Resins, Synthetic
  • Vinyl Compounds
  • trimethylenediamine