Volume 56, Issue 6 pp. 695-696

An oxazol-5(4H)-one from benzyloxy­carbonyl-(Aib)4-OH

Marco Crisma

Marco Crisma

Biopolymer Research Centre, CNR, Department of Organic Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy

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Fernando Formaggio

Fernando Formaggio

Biopolymer Research Centre, CNR, Department of Organic Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy

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Claudio Toniolo

Claudio Toniolo

Biopolymer Research Centre, CNR, Department of Organic Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy

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First published: 30 June 2004
Citations: 4
Marco Crisma, e-mail: [email protected]

Abstract

Benzyl N-[8-(4,4-dimethyl-5-oxo-4,5-dihydrooxazol-2-yl)-2,5,5,8-tetra­methyl-3,6-dioxo-4,7-diazanon-2-yl]­carbamate, C24H34N4O6, an oxazol-5(4H)-one from N-α-benzyloxycarbonyl-(Aib)4-OH (Aib = α-amino­isobutyryl) represents the longest peptide oxazolone so far characterized by X-ray diffraction. The overall geometry of the oxazolone ring compares well with literature data. The Aib(1) and Aib(2) residues are folded into a type III β-bend, while the conformation adopted by Aib(3), preceding the oxazolone moiety, is semi-extended. The disposition of the oxazolone ring relative to the preceding residue is stabilized by C—­H⋯N and C—H⋯O intramolecular interactions.

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