Solid-phase synthesis of constrained terminal and internal lactam peptidomimetics

William L Scott; Jordi Alsina; Joseph H Kennedy; Martin J O'Donnell

doi:10.1021/ol049547z

Solid-phase synthesis of constrained terminal and internal lactam peptidomimetics

Org Lett. 2004 May 13;6(10):1629-32. doi: 10.1021/ol049547z.

Authors

William L Scott¹, Jordi Alsina, Joseph H Kennedy, Martin J O'Donnell

Affiliation

¹ Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, Indiana 46202, USA. wscott@chem.iupui.edu

PMID: 15128253
DOI: 10.1021/ol049547z

Abstract

Lactams are key components of many peptidomimetic structures. Five- and six-membered lactam peptidomimetics with hydrogen or amino acid side chains at the alpha-position can be constructed from peptide precursors during a solid-phase synthesis. There is no significant racemization of remote stereocenters during synthesis.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Cyclization
Lactams / chemistry*
Molecular Mimicry*
Molecular Structure
Peptides, Cyclic / chemical synthesis
Peptides, Cyclic / chemistry

Substances

Lactams
Peptides, Cyclic