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Heterospirocyclic N-(2H-Azirin-3-yl)-L-prolinates: New Dipeptide Synthons


Suter, Giovanni; Stoykova, Svetlana A; Linden, A; Heimgartner, Heinz (2000). Heterospirocyclic N-(2H-Azirin-3-yl)-L-prolinates: New Dipeptide Synthons. Helvetica Chimica Acta, 83:2961-2974.

Abstract

The synthesis of methyl N-(1-aza-6-oxaspiro[2.5]oct-1-en-2-yl)-L-prolinate (1e) has been performed by consecutive treatment of methyl N-[(tetrahydro-2H-pyran-4-yl)thiocarbonyl]-L-prolinate (5) with COCl2, 1,4- diazabicyclo[2.2.2]octane (DABCO), and NaN3 (Scheme 1). As the first example of a novel class of dipeptide synthons, 1e has been shown to undergo the expected reactions with carboxylic acids and thioacids (Scheme 2). The successful preparation of the nonapeptide 16, which is an analogue of the C-terminal nonapeptide of the antibiotic Trichovirin I 1B, proved that 1e can be used in peptide synthesis as a dipeptide building block (Scheme 3). The structure of 7 has been established by X-ray crystal-structure analysis (Figs. 1 and 2).

Abstract

The synthesis of methyl N-(1-aza-6-oxaspiro[2.5]oct-1-en-2-yl)-L-prolinate (1e) has been performed by consecutive treatment of methyl N-[(tetrahydro-2H-pyran-4-yl)thiocarbonyl]-L-prolinate (5) with COCl2, 1,4- diazabicyclo[2.2.2]octane (DABCO), and NaN3 (Scheme 1). As the first example of a novel class of dipeptide synthons, 1e has been shown to undergo the expected reactions with carboxylic acids and thioacids (Scheme 2). The successful preparation of the nonapeptide 16, which is an analogue of the C-terminal nonapeptide of the antibiotic Trichovirin I 1B, proved that 1e can be used in peptide synthesis as a dipeptide building block (Scheme 3). The structure of 7 has been established by X-ray crystal-structure analysis (Figs. 1 and 2).

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2000
Deposited On:28 Oct 2013 11:30
Last Modified:05 Apr 2016 17:05
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, Stiftung für wissenschaftliche Forschung an der Universität Zürich, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/1522-2675(20001108)83:11<2961::AID-HLCA2961>3.0.CO;2-S

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