Issue 0, 1980

Structural studies of azacyclols derived from linear tripeptides

Abstract

N-Benzyloxycarbonyl-L-alanyl-L-phenylalanyl-L-proline p-nitrophenyl ester (4) and its N-p-bromobenzyloxycarbonyl analogue (2) each cyclize in alkaline aqueous medium to give a tricyclic system containing a free hydroxy-group derived from intramolecular addition of NH to amide carbonyl. Both the five-membered rings of the tricyclic system assume an envelope conformation. In the six-membered ring only the carbon atom bearing the cyclolic hydroxy-group is out of the plane of the other ring atoms. The benzylic side-chain of the phenylalanine residue adopts an extended conformation in both azacyclols. The crystal and molecular structures and spectral data for the tricyclic compounds (3) and (5) are reported.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 809-816

Structural studies of azacyclols derived from linear tripeptides

G. Lucente, A. Romeo, S. Cerrini, W. Fedeli and F. Mazza, J. Chem. Soc., Perkin Trans. 1, 1980, 809 DOI: 10.1039/P19800000809

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