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Liquid Chromatographic Resolution of Amino Acid Esters of Acyclovir Including Racemic Valacyclovir on Crown Ether‐Based Chiral Stationary Phases
Author(s) -
Ahn Seong Ae,
Hyun Myung Ho
Publication year - 2015
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.22424
Subject(s) - chemistry , silanol , silica gel , chromatography , chirality (physics) , crown ether , covalent bond , organic chemistry , acetonitrile , prodrug , combinatorial chemistry , catalysis , biochemistry , ion , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Valacyclovir, a potential prodrug for the treatment of patients with herpes simplex and herpes zoster, and its analogs were resolved on two chiral stationary phases (CSPs) based on (3,3’‐diphenyl‐1,1’‐binaphthyl)‐20‐crown‐6 covalently bonded to silica gel. In order to find out an appropriate mobile phase condition, various mobile phases consisting of various organic modifiers in water containing various acidic modifiers were applied to the resolution of valacyclovir and its analogs. When 30% acetonitrile in water containing any of 0.05 M, 0.10 M, or 0.15 M perchloric acid was used as a mobile phase, valacyclovir and its analogs were resolved quite well on the two CSPs with the separation factors (α) in the range of 2.49 ~ 6.35 and resolutions (R S ) in the range of 2.95 ~ 12.21. Between the two CSPs, the CSP containing residual silanol protecting n ‐octyl groups on the silica surface was found to be better than the CSP containing residual silanol groups. Chirality 27:268–273, 2015 . © 2015 Wiley Periodicals, Inc.