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

Title
Chirality Conversion of Dipeptides in the Schiff Bases of Binol Aldehydes with Multiple Hydrogen Bond Donors
Authors
Park, HyunjungHong, JooyeonHam, SihyunNandhakumar, RajuKim, Kwan Mook
Ewha Authors
김관묵
SCOPUS Author ID
김관묵scopus
Issue Date
2009
Journal Title
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
ISSN
0253-2964JCR Link
Citation
vol. 30, no. 2, pp. 409 - 414
Keywords
DeracemizationSchiff baseDipeptideStereoselective recognitionDFT calculation
Publisher
KOREAN CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS; KCI WOS
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.
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자연과학대학 > 화학·나노과학전공 > Journal papers
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