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Chiral recognition based on enantioselective interactions of propranolol enantiomers with cyclosophoraoses isolated from Rhizobium meliloti
Author(s) -
Lee Sanghoo,
Choi Youngjin,
Lee Sangsan,
Jeong Karpjoo,
Jung Seunho
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20010
Subject(s) - chemistry , enantioselective synthesis , enantiomer , propranolol , stereochemistry , chirality (physics) , combinatorial chemistry , organic chemistry , catalysis , medicine , chiral symmetry , nambu–jona lasinio model , physics , quantum mechanics , quark
Cyclosophoraoses isolated from Rhizobium meliloti , as an NMR chiral shift agent, were used to discriminate propranolol enantiomers. Continuous variation plot made from the complex of cyclosophoraoses with propranolol showed that the diastereomeric complex had predominantly 1:1 stoichiometry through UV spectroscopic analysis. The chiral recognition of propranolol enantiomers by cyclosophoraoses was investigated through the determination of binding constant based on the 13 C NMR chemical shift changes. The averaged K obs values from the plots were 55.7 M −1 for ( R )‐(+)‐propranolol and 36.6 M −1 for ( S )‐(–)‐propranolol, respectively. Enantioselectivity (α = K R (+) / K S ( – ) ) of 1.52 was then obtained. Computational calculation also revealed that ( R )‐(+) propranolol was more tightly bound with cyclosophoraose than ( S )‐(–)‐propranolol due to the enhanced van der Waals interaction. Chirality 16:204–210, 2004. © 2004 Wiley‐Liss, Inc.