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Synthesis of tripeptides containing heterocyclic α -amino acids by using heterospirocyclic 3-amino-2H-azirines


Strässler, Christoph; Linden, Anthony; Heimgartner, Heinz (2018). Synthesis of tripeptides containing heterocyclic α -amino acids by using heterospirocyclic 3-amino-2H-azirines. Heterocycles, 97(1):333-354.

Abstract

By using the ‘azirine/oxazolone method’, di- and tripeptides containing six-membered heterocyclic 4-amino-4-carboxylic acids with a piperidine, tetrahydropyran or tetrahydrothiopyran ring have been synthesized. It has been shown that the corresponding heterospirocyclic 3-(N-methyl-N-phenylamino)-2H-azirines are suitable synthons for these heterocyclic α-amino acids. As expected, the presence of these α,α-disubstituted α-amino acids stabilizes β-turn conformations in the prepared tripeptides of type Z-Phe-Xaa-Val-OR.

Abstract

By using the ‘azirine/oxazolone method’, di- and tripeptides containing six-membered heterocyclic 4-amino-4-carboxylic acids with a piperidine, tetrahydropyran or tetrahydrothiopyran ring have been synthesized. It has been shown that the corresponding heterospirocyclic 3-(N-methyl-N-phenylamino)-2H-azirines are suitable synthons for these heterocyclic α-amino acids. As expected, the presence of these α,α-disubstituted α-amino acids stabilizes β-turn conformations in the prepared tripeptides of type Z-Phe-Xaa-Val-OR.

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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:6 March 2018
Deposited On:16 Mar 2018 13:56
Last Modified:04 Dec 2018 15:06
Publisher:Elsevier
ISSN:0385-5414
Funders:Swiss National Science Foundation, Stiftung für wissenschaftliche Forschung an der Universität Zürich, F. Hoffmann-La Roche AG, Basel
OA Status:Closed
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.3987/COM-18-S(T)22
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation
  • : Funder
  • : Grant ID
  • : Project TitleStiftung für wissenschaftliche Forschung an der Universität Zürich
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche AG, Basel

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