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Communication

Effects of Glycosylation of (2S,4R)-4-Hydroxyproline on the Conformation, Kinetics, and Thermodynamics of Prolyl Amide Isomerization

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Neil W. Owens, Craig Braun, Joe D. O'Neil, Kirk Marat, and Frank Schweizer*

Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, R3T 2N2 Canada

J. Am. Chem. Soc., 2007, 129 (38), pp 11670–11671

DOI: 10.1021/ja073488d

Publication Date (Web): September 1, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, schweize@cc.umanitoba.ca

Abstract

Glycosylation (galactosylation) of (2S,4R)-4-hydroxyproline (Hyp) in the peptide mimic N-acetyl-Hyp-N‘-methylamide does not mediate the isomer equilibrium nor the rate of isomerization between the cis- and trans-prolyl amides in water. However, glycosylation of Hyp results in a downfield shift (6.5−8 ppm) of the Cγ atom of proline that is consistent with an enhanced inductive effect. Moreover, NOE experiments on the α-and β-linked glycosylated AcHypNHMe amides indicate proximity between the galactose and pyrrolidine rings. This study strongly suggests that glycosylation of Hyp will have important implications on peptide backbone conformation

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Published In Issue September 26, 2007
Received May 16, 2007

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Communication

Effects of Glycosylation of (2S,4R)-4-Hydroxyproline on the Conformation, Kinetics, and Thermodynamics of Prolyl Amide Isomerization

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Intramolecular Hydrogen Bond-Controlled Prolyl Amide Isomerization in Glucosyl 3′(S)-Hydroxy-5′-hydroxymethylproline Hybrids: Influence of a C-5′-Hydroxymethyl Substituent on the Thermodynamics and Kinetics of Prolyl Amide Cis/Trans Isomerization

Tuning of the Prolyl trans/cis-Amide Rotamer Population by Use of C-Glucosylproline Hybrids

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