Studies on novel peptidomimetics having bi-directional dispositions of hydroxylated D-Pro-Gly motifs anchored on a C2-symmetric iminosugar-based foundation

Chakraborty, T. K. ; Srinivasu, P. ; Kiran Kumar, S. ; Kunwar, A. C. (2002) Studies on novel peptidomimetics having bi-directional dispositions of hydroxylated D-Pro-Gly motifs anchored on a C2-symmetric iminosugar-based foundation Journal of Organic Chemistry, 67 (7). pp. 2093-2100. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo010937y

Related URL: http://dx.doi.org/10.1021/jo010937y

Abstract

A rigid pyrrolidine based scaffold comprising of 2,5-dideoxy-2,5-imino-D-idaric acid (1) is developed. Attachment of peptide strands to the carboxylic groups at both ends of this novel template led to the peptidomimetics 2 and 3. Conformational analysis by NMR studies revealed that compounds 2b, 3b and 2c, 3c take interesting turn structures (C2 symmetric for 2c and 3c) in DMSO-d6 consisting of identical intramolecular hydrogen bonds at two ends between LeuNH → sugar-OH as depicted in structure A, whereas 2a and 3a display structures with regular β-turns with hydrogen bonds between LeuNH → Boc·C=O in one-half of their molecular frameworks (structure B), characteristic of the turn structures commonly observed in "D-Pro-Gly"-containing peptides. These results suggest that a cis hydroxyl group at the 3-position of the proline residue favors a pseudo β-turn-like nine-membered ring structure in hydroxyproline-containing peptides involving an intramolecular hydrogen bond between the hydroxyl and the i + 2 backbone amide.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:20595
Deposited On:20 Nov 2010 13:54
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