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Paper | Special issue | Vol 97, No. 1, 2018, pp.333-354
Published online, 6th March, 2018
DOI: 10.3987/COM-18-S(T)22
Synthesis of Tripeptides Containing Heterocyclic α-Amino Acids by Using Heterospirocyclic 3-Amino-2H-azirines

Christoph Strässler, Anthony Linden, and Heinz Heimgartner*

*Department of Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

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.