From beta-lactams to alpha- and beta-amino acid derived peptides

Amino Acids. 1999;16(3-4):321-43. doi: 10.1007/BF01388175.

Abstract

The potential of beta-lactams as intermediates for the access to alpha- and beta-amino acid-derived peptides is shortly reviewed, with major focus on the technologies developed in our group. The two general strategies lie, on one side, in the oxidative ring expansion of 3-hydroxy beta-lactams to N-carboxy alpha-amino acid anhydrides or Leuch's anhydrides and subsequent coupling with alpha-amino acid esters and, on the other side, in the nucleophilic ring opening of N-Boc-beta-lactams. Both approaches have been successfully applied to the synthesis of alpha,beta-diamino acid, alpha-amino-beta-hydroxy acid, polyhydroxylated alpha-amino acid, alpha,alpha-disubstituted alpha-amino acid, beta-amino acid, beta-amino-alpha-hydroxy acid and beta,beta-disubstituted beta-amino acid derived peptides. Because of the mild reaction conditions needed for the above transformations and the highly stereoselective procedures employed for the construction of the starting beta-lactam ring, the whole process allows the production of optically pure final products.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Amino Acids, Diamino / chemical synthesis*
  • Amino Acids, Diamino / chemistry
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • beta-Lactams / chemistry*

Substances

  • Amino Acids, Diamino
  • Peptides
  • beta-Lactams