Header

UZH-Logo

Maintenance Infos

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.

Statistics

Citations

Dimensions.ai Metrics
18 citations in Web of Science®
20 citations in Scopus®
13 citations in Microsoft Academic
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 23 Oct 2013
0 downloads since 12 months
Detailed statistics

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:18 Apr 2018 11:43
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
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/1522-2675(20010418)84:4<972::AID-HLCA972>3.0.CO;2-M
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche AG, Basel
  • : Funder
  • : Grant ID
  • : Project TitleStiftung für wissenschaftliche Forschung an der Universität Zürich

Download