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A Novel 2H-Azirin-3-amine as a Dipeptide (Aib-Hyp) Synthon


Breitenmoser, Roland A; Hirt, Thomas R; Luykx, Roeland T N; Heimgartner, Heinz (2001). A Novel 2H-Azirin-3-amine as a Dipeptide (Aib-Hyp) Synthon. Helvetica Chimica Acta, 84(4):972-979.

Abstract

The synthesis of methyl (2S,4R)-4-(benzyloxy)-N-(2,2-dimethyl-2H-azirin-3-yl)prolinate (10), a novel 2H-azirin-3-amine ('3-amino-2H-azirine'), is described (Scheme 1). The reaction of methyl (2S,4R)-N-(2- methylpropanoyl)-4-(benzyloxy)prolinate (7) with Lawesson reagent gave methyl (2S,4R)-4-(benzyloxy)-N-[2-(methylthio)propanoyl]prolinate (8) and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to 10. The use of 10 as a building block of the dipeptide Aib-Hyp (Aib = 2- aminoisobutyric acid, Hyp = (2S,4R)-4-hydroxyproline) is demonstrated by the syntheses of several model peptides (Scheme 2 and Table). The benzyl protecting group of the 4-OH function in Hyp in the model peptides has been removed in good yields.

Abstract

The synthesis of methyl (2S,4R)-4-(benzyloxy)-N-(2,2-dimethyl-2H-azirin-3-yl)prolinate (10), a novel 2H-azirin-3-amine ('3-amino-2H-azirine'), is described (Scheme 1). The reaction of methyl (2S,4R)-N-(2- methylpropanoyl)-4-(benzyloxy)prolinate (7) with Lawesson reagent gave methyl (2S,4R)-4-(benzyloxy)-N-[2-(methylthio)propanoyl]prolinate (8) and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to 10. The use of 10 as a building block of the dipeptide Aib-Hyp (Aib = 2- aminoisobutyric acid, Hyp = (2S,4R)-4-hydroxyproline) is demonstrated by the syntheses of several model peptides (Scheme 2 and Table). The benzyl protecting group of the 4-OH function in Hyp in the model peptides has been removed in good yields.

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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:2001
Deposited On:23 Oct 2013 06:41
Last Modified:05 Apr 2016 17:03
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Stiftung für wissenschaftliche Forschung an der Universität Zürich
Publisher DOI:https://doi.org/10.1002/1522-2675(20010418)84:4<972::AID-HLCA972>3.0.CO;2-M

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