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http://dx.doi.org/10.5012/bkcs.2009.30.2.409

Chirality Conversion of Dipeptides in the Schiff Bases of Binol Aldehydes with Multiple Hydrogen Bond Donors  

Park, Hyun-Jung (Bio-Chiral Lab, Department of Chemistry and Nano Sciences, Ewha Womans University)
Hong, Joo-Yeon (Department of Chemistry, Sookmyung Women’s University)
Ham, Si-Hyun (Department of Chemistry, Sookmyung Women’s University)
Nandhakumar, Raju (Bio-Chiral Lab, Department of Chemistry and Nano Sciences, Ewha Womans University)
Kim, Kwan-Mook (Bio-Chiral Lab, Department of Chemistry and Nano Sciences, Ewha Womans University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.2, 2009 , pp. 409-414 More about this Journal
Abstract
Novel binol aldehydes derivatized at 2' hydroxy position with both uryl and acetamide groups (2), and diuryl groups (3) have been synthesized. Both were designed for streospecific binding and chirality conversion of general dipeptides with support of multiple hydrogen bonding donor sites in the receptors. The receptors, 2 and 3, converted the chirality of N-terminal amino acids of peptides such as Ala-Gly, Met-Gly, Leu-Gly and His-Gly with stereoselectivity on D-form over L-form. The stereoselectivity ratios were in the range of 5-11, somewhat higher than those of the binol receptor with mono uryl group (1). The DFT calculation at the B3LYP/6-31G$^*$//MPWB1K/6-31G$^*$ level revealed that 3-D-Ala-Gly was 2.2 kcal/mol more stable than 3-L-Ala-Gly. The considerable steric hindrance between the methyl group of the alanine and the imine CH moiety of the receptor seems to be the main contributing factor for the thermodynamic preference.
Keywords
Deracemization; Schiff base; Dipeptide; Stereoselective recognition; DFT calculation;
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