An access to aza-Freidinger lactams and E-locked analogs

Philipp A Ottersbach; Janina Schmitz; Gregor Schnakenburg; Michael Gütschow

doi:10.1021/ol3030583

An access to aza-Freidinger lactams and E-locked analogs

Org Lett. 2013 Feb 1;15(3):448-51. doi: 10.1021/ol3030583. Epub 2013 Jan 15.

Authors

Philipp A Ottersbach¹, Janina Schmitz, Gregor Schnakenburg, Michael Gütschow

Affiliation

¹ Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121 Bonn, Germany.

PMID: 23320486
DOI: 10.1021/ol3030583

Abstract

Freidinger lactams, possessing a peptide bond configuration locked to Z, are important key elements of conformationally restricted peptidomimetics. In the present work, the C(α)H(i+1) unit has been replaced by N, leading to novel aza-Freidinger lactams. A synthesis to corresponding building blocks and their E-locked analogs is introduced. The versatile buildings blocks reported here are expected to serve as useful elements in peptide synthesis.

Publication types

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

MeSH terms

Aza Compounds / chemical synthesis*
Aza Compounds / chemistry
Cysteine Proteases / drug effects
Lactams / chemical synthesis*
Lactams / chemistry
Molecular Structure
Peptides / chemical synthesis*
Peptides / chemistry
Stereoisomerism

Substances

Aza Compounds
Lactams
Peptides
Cysteine Proteases