Separation of Alkyne Enantiomers by Chiral Column HPLC Analysis of Their Cobalt-Complexes.
Separation of the enantiomers of new chiral alkynes in strategic syntheses and bioorthogonal studies is always problematic. The chiral column high-performance liquid chromatography (HPLC) method in general could not be directly used to resolve such substrates, since the differentiation of the alkyne segment with the other alkane/alkene segment is not significant in the stationary phase, and the alkyne group is not a good UV chromophore. Usually, a pre-column derivatization reaction with a tedious workup procedure is needed. Making use of easily-prepared stable alkyne-cobalt-complexes, we developed a simple and general method by analyzing the in situ generated cobalt-complex of chiral alkynes using chiral column HPLC. This new method is especially suitable for the alkynes without chromophores and other derivable groups.
School of Chemistry and Material Science, Shanxi Normal University, 1 Gongyuan Street, Linfen, Shanxi 041004, China. liuqy@sxnu.edu.cn.
Qiaoyun
Q
Liu
School of Chemistry and Material Science, Shanxi Normal University, 1 Gongyuan Street, Linfen, Shanxi 041004, China. 214111062@stu.sxnu.edu.cn.|State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China. 214111062@stu.sxnu.edu.cn.
Jing
J
Wang
School of Chemistry and Material Science, Shanxi Normal University, 1 Gongyuan Street, Linfen, Shanxi 041004, China. lijunfei@sxnu.edu.cn.
Junfei
J
Li
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China. wangxiaolei@imm.ac.cn.
Xiaolei
X
Wang
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China. lushichao@imm.ac.cn.
Shichao
S
Lu
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China. lanthanum1979@gmail.com.
Xuan
X
Li
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China. ylgong@imm.ac.cn.
Yaling
Y
Gong
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China. xushu@imm.ac.cn.
Shu
S
Xu
D000480:Alkynes / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003035:Cobalt / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D003035:Cobalt
HPLC; alkyne; chiral column; cobalt complex; resolution