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N-Benzhydryl-glycolamide: the first protecting group in peptide synthesis with a strong conformational bias (Articolo in rivista)

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N-Benzhydryl-glycolamide: the first protecting group in peptide synthesis with a strong conformational bias (Articolo in rivista) (literal)

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Alternative label

Crisma M., Formaggio F., Ruzza P., Calderan A., Elardo S., Borin G., Toniolo C. (2003)
N-Benzhydryl-glycolamide: the first protecting group in peptide synthesis with a strong conformational bias
in Biopolymers (Print)
(literal)

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Crisma M., Formaggio F., Ruzza P., Calderan A., Elardo S., Borin G., Toniolo C. (literal)

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Citazioni WOS: 5; Impact Factor 2003: 2.733; M. Crisma: \"Corresponding author\"; P. Ruzza: Coautore; A. Calderan: Coautore (literal)

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Rivista

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We have synthesized and examined the preferred conformation of a set of N-benzhydryl-glycolamide esters from Nalpha-protected (or Nalpha-blocked)alpha-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 Nalpha-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. (literal)

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Institute of Biomolecular Chemistry, Padova Unit, CNR, Department of Organic Chemistry, University of Padova, 35131 Padova, Italy (literal)

Titolo

N-Benzhydryl-glycolamide: the first protecting group in peptide synthesis with a strong conformational bias (literal)

Abstract

We have synthesized and examined the preferred conformation of a set of N-benzhydrylglycolamide esters from N-alpha-protected (or N-alpha-blocked) alpha-amino acids. Experiments were performed in CDCl3 solution by Fourier transform infrared absorption and H-1-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. (literal)

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