Stereoselective synthesis of (R)- and (S)-1,2-diazetidine-3-carboxylic acid derivatives for peptidomimetics

Matthew Nutter; Henry Stone; Michael Shipman; Stefan Roesner

doi:10.1039/d4ob00278d

Stereoselective synthesis of (R)- and (S)-1,2-diazetidine-3-carboxylic acid derivatives for peptidomimetics

Org Biomol Chem. 2024 Apr 17;22(15):2974-2977. doi: 10.1039/d4ob00278d.

Authors

Matthew Nutter¹, Henry Stone¹, Michael Shipman¹, Stefan Roesner¹

Affiliation

¹ Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, UK. [email protected].

PMID: 38533707
DOI: 10.1039/d4ob00278d

Abstract

The stereoselective synthesis of both enantiomers of N-protected 1,2-diazetidine-3-carboxylic acid (aAze) from homochiral glycidol is described. Orthogonal protection of this novel cyclic α-hydrazino acid allows for selective functionalisation at either N^γ or N^δ. This novel peptidomimetic building block was incorporated into the pseudotripeptides Gly-γaAze-Ala and Gly-δaAze-Ala.