Enzymatic synthesis of phosphocarnitine, phosphogabob and fosfomycin.
Phosphocarnitine was conveniently obtained from easily available diethyl 3-chloro-2-oxopropanephosphonates, followed by subsequent reduction, Mucor miehei lipase (IM) mediated resolution, amination and dealkylation. Candida antarctica lipase B (CALB) served as an effective biocatalyst in the resolution of several 1- or 2-hydroxyalkanephosphonates. The chlorine atom in different positions on the molecules greatly affected their enantioselectivity. CALB also showed satisfactory enantioselectivity toward those molecules bearing an azido moiety. Both enantiomers of phosphogabob and fosfomycin were also prepared via CALB-mediated resolution as the key step.
Wang
Ke
K
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Zhang
Yonghui
Y
Yuan
Chengye
C
D000473:Alkanes / Q000138:chemical synthesis*; D002175:Candida / Q000201:enzymology; D002331:Carnitine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D002384:Catalysis; D005578:Fosfomycin / Q000138:chemical synthesis*; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism; D008956:Models, Chemical; D015394:Molecular Structure; D009089:Mucor / Q000201:enzymology; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013816:Thermodynamics
D000473:Alkanes; D005656:Fungal Proteins; D009943:Organophosphorus Compounds; C485025:phosphocarnitine; C485028:phosphogabob; D005578:Fosfomycin; D008049:Lipase; C431349:lipase B, Candida antarctica; D002331:Carnitine