Solid-phase synthesis of amino- and carboxyl-functionalized unnatural alpha-amino acid amides

Org Lett. 2009 Aug 20;11(16):3558-61. doi: 10.1021/ol901279v.

Abstract

A new solid-phase synthesis efficiently incorporates three different substituents (from R(1)-X, R(2)-CO(2)H, and R(3)-NH(2)) into a glycine-based peptidomimetic scaffold. The synthetic sequence is general and is typically accomplished in >50% overall isolated yield. Alkylating agents with a range of reactivities and normal and branched primary amines give good results. Utility was demonstrated by the synthesis of a series of protected phosphotyrosine mimetics.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Glycine / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amides
  • Amino Acids
  • Glycine