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

Nutter, M ORCID: 0009-0007-8871-5295, Stone, H ORCID: 0009-0009-0557-8833, Shipman, M ORCID: 0000-0002-3349-5594 and Roesner, S ORCID: 0000-0003-2143-4708 (2024) Stereoselective synthesis of (R)- and (S)-1,2-diazetidine-3-carboxylic acid derivatives for peptidomimetics. Organic & Biomolecular Chemistry, 22 (15). pp. 2974-2977. ISSN 1477-0520

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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 Nγ or Nδ. This novel peptidomimetic building block was incorporated into the pseudotripeptides Gly-γaAze-Ala and Gly-δaAze-Ala.

Item Type:	Article
Uncontrolled Keywords:	0304 Medicinal and Biomolecular Chemistry; 0305 Organic Chemistry; Organic Chemistry
Subjects:	Q Science > QD Chemistry R Medicine > RS Pharmacy and materia medica
Divisions:	Pharmacy and Biomolecular Sciences
Publisher:	Royal Society of Chemistry
Date of acceptance:	24 March 2024
Date of first compliant Open Access:	23 April 2024
Date Deposited:	23 Apr 2024 09:28
Last Modified:	04 Jul 2025 12:45
DOI or ID number:	10.1039/D4OB00278D
URI:	https://researchonline.ljmu.ac.uk/id/eprint/23104

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