N-benzhydryl-glycolamide: the first protecting group in peptide synthesis with a strong conformational bias |
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Authors: | Crisma Marco Formaggio Fernando Ruzza Paolo Calderan Andrea Elardo Stefano Borin Gianfranco Toniolo Claudio |
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Institution: | Institute of Biomolecular Chemistry, Padova Unit, CNR, Department of Organic Chemistry, University of Padova, Italy. marco.crisma@unipd.it |
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Abstract: | We have synthesized and examined the preferred conformation of a set of N-benzhydryl-glycolamide esters from N(alpha)-protected (or N(alpha)-blocked) alpha-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(alpha)-acylated alpha-aminoacyl esters has a marked tendency to fold into a beta-turn conformation, the nature of which is dictated by the structural propensity of the amino acid constituent at the i+1 position. |
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