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Facile determination of the absolute configurations of α-hydroxy acids by chiral derivatization coupled with liquid chromatography-mass spectrometry analysis.
MedLine Citation:
PMID:  23261293     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
α-Hydroxy acids are commonly encountered in natural bioactive molecules. For convenient determination of the absolute configurations of α-hydroxy acids, a simple method, named the "O-Marfey method" was developed using a chiral derivatization strategy with (1-fluoro-2,4-dinitrophenyl-5)-l-alanine amide (l-FDAA). The liquid chromatography-mass spectrometry (LC-MS) analysis of the derivatives clearly determined the absolute configurations of various α-hydroxy acids based on their elution times and sequences. This new method is operationally simple with short reaction time and sensitive enough for application at a sub-milligram scale without any purification. This method also enables the simultaneous chirality analysis of α-hydroxy acids and α-amino acids. The absolute configuration of a natural depsipeptide bearing an α-hydroxy acid and α-amino acids was successfully determined by our O-Marfey application.
Authors:
Kyuho Moon; Chaemin Lim; Sanghee Kim; Dong-Chan Oh
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-12-5
Journal Detail:
Title:  Journal of chromatography. A     Volume:  -     ISSN:  1873-3778     ISO Abbreviation:  J Chromatogr A     Publication Date:  2012 Dec 
Date Detail:
Created Date:  2012-12-24     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9318488     Medline TA:  J Chromatogr A     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2012 Elsevier B.V. All rights reserved.
Affiliation:
Natural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea.
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