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2. A β-lactam route to short peptide segments related to angiotensin-converting enzyme (ACE) inhibitors

Author

Mikel Oiarbide, Claudio Palomo, Giuseppe Tomasi Sciano, Iñaki Ganboa, and José I. Miranda

Subjects
chemistry.chemical_classification, biology, Stereochemistry, Organic Chemistry, Angiotensin-converting enzyme, Peptide, respiratory system, Ring (chemistry), Cycloaddition, Acid anhydride, lcsh:QD241-441, chemistry.chemical_compound, Carboxylation, chemistry, lcsh:Organic chemistry, biology.protein, Lactam, medicine, Enalapril, medicine.drug
Abstract

The stereocontrolled synthesis of the Angiotensin Converting Enzyme (ACE) inhibitor enalapril is reported. The key transformation of the synthesis is a formal carboxylation of imines, which lies in the sequence: imine-ketene (2+2) cycloaddition reaction, ring expansion of the resulting 3- hydroxy β-lactam to a N-carboxy α-amino acid anhydride (NCA), and final opening of the NCA with alcohols.

Published
2002

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