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Elucidation of vancomycin's enantioselective binding site using its copper complex
Author(s) -
Nair Usha B.,
Chang Samuel S.C.,
Armstrong Daniel W.,
Rawjee Yasir Y.,
Eggleston Drake S.,
McArdle James V.
Publication year - 1996
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/(sici)1520-636x(1996)8:8<590::aid-chir9>3.0.co;2-d
Subject(s) - chemistry , enantioselective synthesis , copper , vancomycin , moiety , chirality (physics) , amine gas treating , dissociation (chemistry) , stereochemistry , enantiomer , combinatorial chemistry , organic chemistry , catalysis , staphylococcus aureus , bacteria , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , biology , genetics
Vancomycin forms a stable complex with Cu 2− in neutral aqueous solutions. The enantioselectivity of native vancomycin was compared to that of the copper‐vancomycin complex using capillary electrophoresis (CE). There were significant differences in their enantioselectivities. This can be attributed to the fact that copper ion coordinates with some of the same functional groups in vancomycin that are essential for chiral recognition and enantioresolution. An amine moiety that provides one of the more important enantioselective interactions was identified. This chiral interaction site was illustrated using a color‐coded, space‐filling model of the X‐ray crystal structure of the copper‐vancomycin complex. Successful enantioselective interactions at lower pHs were attributed to the partial dissociation of the copper‐vancomycin complex. Chirality 8:590–595, 1996. © 1997 Wiley‐Liss, Inc.