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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Matthew Nutter,

‡^a Henry Stone,

‡^a Michael Shipman

^a and Stefan Roesner

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, UK
E-mail: s.roesner@warwick.ac.uk

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.

Download options Please wait...

Supplementary files

Supplementary information PDF (3439K)

Article information

DOI: https://doi.org/10.1039/D4OB00278D
Article type: Communication
Submitted: 21 Feb 2024
Accepted: 24 Mar 2024
First published: 25 Mar 2024
This article is Open Access

Download Citation

Org. Biomol. Chem., 2024,22, 2974-2977

Permissions

Request permissions

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

M. Nutter, H. Stone, M. Shipman and S. Roesner, Org. Biomol. Chem., 2024, 22, 2974 DOI: 10.1039/D4OB00278D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements