PMID: 11925214Apr 2, 2002Paper

Studies on novel peptidomimetics having bi-directional dispositions of hydroxylated D-Pro-Gly motifs anchored on a C(2)-symmetric iminosugar-based foundation

The Journal of Organic Chemistry
T K ChakrabortyA C Kunwar

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 (C(2) symmetric for 2c and 3c) in DMSO-d(6) 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 beta-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 beta-turn-like nine-membered ring structure in hydroxyproline-containing peptides involving an intramolecular hydrogen bond between the hydroxyl and the i + 2 backbone amide.

References

Aug 4, 1995·Journal of Medicinal Chemistry·M A RampyR E Counsell
Jan 1, 1994·Methods in Enzymology·A J Wand, J H Short

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Citations

Sep 1, 2005·Glycoconjugate Journal·Tushar Kanti ChakrabortyBajjuri Krishna Mohan
May 19, 2005·Chemical Communications : Chem Comm·K Krishna PrasadSandeep Verma
May 2, 2012·Chemical Society Reviews·Corien de GraaffRomano V A Orru
Mar 8, 2014·Beilstein Journal of Organic Chemistry·Gijs KoopmanschapRomano Va Orru
Feb 27, 2013·Chemical Communications : Chem Comm·Adam J LoweFrederick M Pfeffer
Aug 30, 2013·Organic & Biomolecular Chemistry·Madhuri VangalaDilip D Dhavale
Oct 9, 2004·The Journal of Organic Chemistry·T K ChakrabortyA C Kunwar
May 19, 2012·Organic Letters·Kiran Kumar Pulukuri, Tushar Kanti Chakraborty
Jan 13, 2005·Journal of the American Chemical Society·Timothy M ChapmanBenjamin G Davis

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