Selective deprotection of phthalyl protected amines

• Published in: Tetrahedron letters Vol. 37; no. 42; pp. 7469 - 7472
• Main Authors: Costello, Colleen A., Kreuzman, Adam J., Zmijewski, Milton J.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 14.10.1996; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/0040-4039(96)01752-2

Phthalyl amidase selectively deprotects phthalimido groups under very mild aqueous conditions in a one-pot reaction to produce phthalic acid and the free amine. The enzyme has been shown to deprotect several primary amines of distinctly different structure, and exhibits chiral selectivity when the substrate contains extensive β-branching. The enzyme has a definite requirement for ortho positioning of the functional groups on a fixed axis of rotation. Phthalyl amidase selectively deprotects phthalimido groups under very mild aqueous conditions in a one-pot reaction to produce phthalic acid and the free amine. The enzyme has been shown to deprotect several primary amines of distinctly different structure, and exhibits chiral selectivity when the substrate contains extensive β-branching. The enzyme has a definite requirement for ortho positioning of the functional groups on a fixed axis of rotation.