N-benzhydryl-glycolamide: The first protecting group in peptide synthesis with a strong conformational bias
✍ Scribed by Marco Crisma; Fernando Formaggio; Paolo Ruzza; Andrea Calderan; Stefano Elardo; Gianfranco Borin; Claudio Toniolo
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 2003
- Tongue
- English
- Weight
- 144 KB
- Volume
- 71
- Category
- Article
- ISSN
- 0006-3525
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✦ Synopsis
Abstract
We have synthesized and examined the preferred conformation of a set of N‐benzhydryl‐glycolamide esters from N^α^‐protected (or N^α^‐blocked) α‐amino acids. Experiments were performed in CDCl~3~ solution by Fourier transform infrared absorption and ^1^H‐NMR techniques, and in the crystalline state by x‐ray diffraction. The results of our analysis strongly support the view that this type of N^α^‐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