ChemInform Abstract: Heterospirocyclic N‐(2H‐Azirin‐3‐yl)‐L‐prolinates: New Dipeptide Synthons.

Abstract

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A novel 2H-azirin-3-amine as a synthon for a sulfur-containing dipeptide segment

“…Like other α,α-disubstituted α-amino acids, the presence of 5 forces peptides to form β-turns [12] or helical conformations. In our studies towards the synthesis of such sterically congested oligopeptides with a helical conformation by using the 'azirine/oxazolone method' [25][26][27][28][29], we introduced N-(2,2-dimethyl-2H-azirin-3-yl)proline methyl ester as a dipeptide (Aib-Pro) synthon [30][31][32] as well as other dipeptide (Xaa-Pro) synthons, including those with Xaa being a heterocyclic α-amino acid [13,33,34]. The aim of the present study was the synthesis of (S)-N-(1-aza-6-thiaspiro[2.5]oct-1-en-2-yl)proline methyl ester (1c) and its use as a…”