Premium
Measurement of Enantiomeric Excess by Kinetic Resolution and Mass Spectrometry
Author(s) -
Guo Jianhua,
Wu Jiangyue,
Siuzdak Gary,
Finn M. G.
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990614)38:12<1755::aid-anie1755>3.0.co;2-q
Subject(s) - chemistry , mass spectrometry , derivatization , enantiomer , acylation , enantiomeric excess , kinetic resolution , electrospray ionization , electrospray , chromatography , resolution (logic) , organic chemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science
New applications for your mass spectrometer —use it to measure enantiomeric excess! The enantiomeric content of very small quantities of chiral alcohols and amines has been determined by derivatization with chiral acylating agents in which mass is correlated to absolute configuration. The resultant esters and amides were then analyzed by electrospray ionization mass spectrometry (ESI‐MS; shown schematically). The technique requires surprisingly low levels of diastereoselectivity in the acylation step, and is therefore generally applicable.