ISSN:
0947-3440
Keywords:
2-Fluoromevalonate
;
Methylmevalonates
;
Mevalonate kinase
;
Chirality
;
Configuration determination
;
Molecular recognition
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Both 2-methyl- and 2-fluoromevalonate are alternative substrates of mevalonate kinase, but only the fluorinated compound is phorphorylated stereospecifically with respect to the chiral C-2. The absolute configuration of the racemic pairs of 2-fluoromevalonate is deduced from 1H- and 13C-NMR data. The fluorine substituent shifts the equilibrium between the conformers of mevalolactone. Coupling constants found experimentally for 2-fluoromevalonate are calculated satisfactorily with INDO-MO data. Enzymatic analysis of components of the racemic pairs of 2-fluoromevalonate with mevalonate kinase combined with NMR data yield the absolute configuration of the enzymatically active steroisomer, (2R,3R)-2-fluoromevalonate.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970320
Permalink