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A novel 2H-azirin-3-amine as a synthon for a sulfur containing dipeptide segment


Stoykova, Svetlana A; Linden, Anthony; Heimgartner, Heinz (2014). A novel 2H-azirin-3-amine as a synthon for a sulfur containing dipeptide segment. Journal of Sulfur Chemistry, 35(1):14-23.

Abstract

Starting with tetrahydro-2H-thiopyran-4-carboxylic acid and methyl prolinate, the novel 2H-azirin-3-amine (S)-N-(1-aza-6-thiaspiro[2.5]oct-1-en-2-yl)proline methyl ester was synthesized. In reactions with benzoic acid, thiobenzoic acid and Boc-valine, respectively, its usefulness as a synthon for the dipeptide (S)-N-[(4-aminotetrahydro-2H-thiopyran-4-yl)carbonyl]proline in peptide synthesis was demonstrated.

Abstract

Starting with tetrahydro-2H-thiopyran-4-carboxylic acid and methyl prolinate, the novel 2H-azirin-3-amine (S)-N-(1-aza-6-thiaspiro[2.5]oct-1-en-2-yl)proline methyl ester was synthesized. In reactions with benzoic acid, thiobenzoic acid and Boc-valine, respectively, its usefulness as a synthon for the dipeptide (S)-N-[(4-aminotetrahydro-2H-thiopyran-4-yl)carbonyl]proline in peptide synthesis was demonstrated.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2014
Deposited On:15 May 2013 14:04
Last Modified:05 Apr 2016 16:47
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:Swiss National Science Foundation
Publisher DOI:https://doi.org/10.1080/17415993.2013.774401

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