title: Qualitative and quantitative analysis of enantiomers by mass spectrometry: application of a simple chiral chloride probe via rapid in-situ reaction.
abstract: A tandem mass spectrometry method for high-sensitivity qualitative and quantitative discrimination of chiral amino compounds is conducted. The method is based on a chemical derivation process that uses a simple reagent, L-1-(phenylsulfonyl)pyrrolidine-carbonyl chloride, as the probe. The method is applicable in both organic solutions and biological conditions. Twenty-one pairs of enantiomer containing amino acids, amino alcohols, and amines are used to produce diastereomers using the probe via in situ reaction for 20 s at room temperature. The resulting diastereomers are successfully recognized based on the relative peak intensities of their fragments in positive mode, with the chiral recognition ability values ranging from 0.35 to 3.83. The L/D ratio of Pro spiked at different concentrations (enantiomeric excess) in both acetonitrile and dog plasma is determined by establishing calibration curves. This method achieves a lower limit of quantification of 50 pmol in analyzing amino acids using an extract ion chromatograph. The relative standard deviation for both qualitative and quantitative results is <5%. Thus, the present method is demonstrated as a new and practical technique of rapidly and sensitively determining enantiomers of amino compounds.
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China.
authors.forename: Lin
authors.initials: L
authors.lastname: Wang
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China.
authors.forename: Yunfeng
authors.initials: Y
authors.lastname: Chai
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China.
authors.forename: Zhangqin
authors.initials: Z
authors.lastname: Ni
authors.affiliation: College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, Zhejiang, PR China.
authors.forename: Lu
authors.initials: L
authors.lastname: Wang
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China.
authors.forename: Ruilin
authors.initials: R
authors.lastname: Hu
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China. Electronic address: panyuanjiang@zju.edu.cn.
authors.forename: Yuanjiang
authors.initials: Y
authors.lastname: Pan
authors.affiliation: College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, Zhejiang, PR China. Electronic address: suncuirong@zju.edu.cn.
authors.forename: Cuirong
authors.initials: C
authors.lastname: Sun
mesh_terms: D000097:Acetonitriles / Q000032:analysis / Q000737:chemistry; D000588:Amines / Q000032:analysis* / Q000737:chemistry*; D000596:Amino Acids / Q000032:analysis / Q000737:chemistry; D000605:Amino Alcohols / Q000032:analysis / Q000737:chemistry; D000818:Animals; D004285:Dogs; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D053719:Tandem Mass Spectrometry
chemical_list: D000097:Acetonitriles; D000588:Amines; D000596:Amino Acids; D000605:Amino Alcohols; D011759:Pyrrolidines; D013449:Sulfonamides; C032159:acetonitrile
keywords: Chiral probe; Chiral recognition; Mass spectrometry; Qualify and quantify.