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Stereoselective synthesis of (R)- and (S)-1,2-diazetidine-3-carboxylic acid derivatives for peptidomimetics
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Nutter, Matthew, Stone, Henry, Shipman, Michael and Roesner, Stefan (2024) Stereoselective synthesis of (R)- and (S)-1,2-diazetidine-3-carboxylic acid derivatives for peptidomimetics. Organic & Biomolecular Chemistry . doi:10.1039/D4OB00278D ISSN 1477-0520. (In Press)
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WRAP-stereoselective-synthesis-(R)-(S)-1,2-diazetidine-3-carboxylic-acid-derivatives-peptidomimetics-2024.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution. Download (228Kb) | Preview |
Official URL: http://dx.doi.org/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 Nγ or Nδ. This novel peptidomimetic building block was incorporated into the pseudotripeptides Gly-γaAze-Ala and Gly-δaAze-Ala
Item Type: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
Library of Congress Subject Headings (LCSH): | Enantiomers , Chirality , Carboxylic acids -- Derivatives | |||||||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | |||||||||
Publisher: | Royal Society of Chemistry | |||||||||
ISSN: | 1477-0520 | |||||||||
Official Date: | 25 March 2024 | |||||||||
Dates: |
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DOI: | 10.1039/D4OB00278D | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | In Press | |||||||||
Access rights to Published version: | Open Access (Creative Commons) | |||||||||
Date of first compliant deposit: | 26 March 2024 | |||||||||
Date of first compliant Open Access: | 28 March 2024 | |||||||||
RIOXX Funder/Project Grant: |
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