Induction of chirality: experimental evidence of atropisomerism in azapeptides

Philipp A Ottersbach; Gregor Schnakenburg; Michael Gütschow

doi:10.1039/c2cc31161e

Induction of chirality: experimental evidence of atropisomerism in azapeptides

Chem Commun (Camb). 2012 Jun 11;48(46):5772-4. doi: 10.1039/c2cc31161e. Epub 2012 May 2.

Authors

Philipp A Ottersbach¹, Gregor Schnakenburg, Michael Gütschow

Affiliation

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

PMID: 22552375
DOI: 10.1039/c2cc31161e

Abstract

Methylation of the peptide bond in model azadipeptides leads to the E configuration and hence to atropisomerism due to a restricted rotation around the N-N axis.

Publication types

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

MeSH terms

Aza Compounds / chemistry*
Methylation
Nitrogen / chemistry
Peptides / chemistry*
Stereoisomerism

Substances

Aza Compounds
Peptides
Nitrogen