N-benzhydryl-glycolamide: The first protecting group in peptide synthesis with a strong conformational bias

• Published in: Biopolymers Vol. 71; no. 1; pp. 17 - 27
• Main Authors: Crisma, Marco, Formaggio, Fernando, Ruzza, Paolo, Calderan, Andrea, Elardo, Stefano, Borin, Gianfranco, Toniolo, Claudio
• Format: Journal Article
• Language: English
• Published: New York Wiley Subscription Services, Inc., A Wiley Company 2003
• Subjects: Benzhydryl Compounds; benzhydryl-glycolamide esters; conformational analysis; Crystallography, X-Ray; depsipeptides; Dimethyl Sulfoxide; folding inducer; Indicators and Reagents; ir absorption; Magnetic Resonance Spectroscopy; Models, Molecular; NMR; Peptides - chemical synthesis; Peptides - chemistry; protecting group; Protein Conformation; Spectroscopy, Fourier Transform Infrared; x-ray diffraction; α-amino isobutyric acid derivative; β-turn
• ISSN: 0006-3525; 1097-0282
• DOI: 10.1002/bip.10373

We have synthesized and examined the preferred conformation of a set of N‐benzhydryl‐glycolamide esters from Nα‐protected (or Nα‐blocked) α‐amino acids. Experiments were performed in CDCl3 solution by Fourier transform infrared absorption and 1H‐NMR techniques, and in the crystalline state by x‐ray diffraction. The results of our analysis strongly support the view that this type of Nα‐acylated α‐aminoacyl esters has a marked tendency to fold into a β‐turn conformation, the nature of which is dictated by the structural propensity of the amino acid constituent at the i+1 position. © 2003 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 71:17–27, 2003