Albendazole sulfoxide enantiomers: Preparative chiral separation and absolute stereochemistry

被引：23

作者：

Lourenco, Tiago C. ^{[1
]}

Batista, Joao M., Jr. ^{[2
]}

Furlan, Maysa ^{[2
]}

He, Yanan ^{[3
]}

Nafie, Laurence A. ^{[4
]}

Santana, Cesar C. ^{[5
]}

Cass, Quezia B. ^{[1
]}

机构：

[1] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP, Brazil

[2] Sao Paulo State Univ UNESP, Dept Organ Chem, BR-14800900 Araraquara, SP, Brazil

[3] BioTools Inc, Jupiter, FL 33458 USA

[4] Syracuse Univ, Dept Chem, Syracuse, NY 13244 USA

[5] State Univ Campinas UNICAMP, Sch Chem Engn, Dept Biotechnol Proc, BR-13083970 Campinas, SP, Brazil

来源：

JOURNAL OF CHROMATOGRAPHY A | 2012年 / 1230卷

基金：

巴西圣保罗研究基金会;

关键词：

Albendazole sulfoxide; Simulated moving bed chromatography; VARICOL process; Multimilligram enantiomeric separation; Vibrational circular dichroism; Absolute configuration; VIBRATIONAL CIRCULAR-DICHROISM; MOVING-BED CHROMATOGRAPHY; STATIONARY PHASES; METHYL SULFOXIDE; CONFIGURATION; ENANTIOSEPARATION; SPECTROSCOPY; RESOLUTION; ISOTHERMS; MOLECULES;

D O I：

10.1016/j.chroma.2012.01.070

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The enantiomeric separation of albendazole sulfoxide was carried out by simulated moving bed chromatography with variable zones (VARICOL). An overall recovery of 97% was achieved and enantiomeric ratios of 99.5% for raffinate and 99.0% for extract were attained. A total of 880 mg of (+)-albendazol sulfoxide and 930 mg of its antipode were collected after 55 cycles or 11 h of process, resulting in a mass rate of 2 g/day. Furthermore the absolute configuration of the enantiopure compounds was determined for the first time by vibrational circular dichroism (VCD) with the aid of theoretical calculations as (-)-(S) and (+)-(R)-albendazole sulfoxide. (C) 2012 Elsevier B.V. All rights reserved.

引用

页码：61 / 65

页数：5

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