Chemoenzymatic synthesis of phosphocarnitine enantiomers.
Racemic phosphocarnitine 3 has been synthesized starting from diethyl 3-chloro-2-oxopropanephosphonate 4 in three steps involving reduction of 4 to the corresponding 2-hydroxyphosphonate 5, conversion of the latter to phosphonic acid 6, and final reaction with trimethylamine, affording the trimethylammonium salt of 3. Baker's yeast reduction of 4 and enzymatic kinetic resolution of (+/-)-5 afforded the enantiomerically pure precursors of phosphocarnitine, (R)-(+)-5 and (S)-(-)-5, which were converted to (S)-(-)- and (R)-(+)-phosphocarnitine 3, respectively.
Mikołajczyk
Marian
M
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, 90-363 Łódź, Sienkiewicza 112, Poland. marmikol@bilbo.cbmm.lodz.pl
ŁUczak
Jerzy
J
Kiełbasinski
Piotr
P
D002331:Carnitine / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D010766:Phosphorylation; D012441:Saccharomyces cerevisiae / Q000201:enzymology*; D013237:Stereoisomerism
D002331:Carnitine