Enzymic acylation of methyl D- and L-glycopyranosides: influence of the 3-hydroxyl group.
Porcine pancreatic (PPL), Candida cylindracea (CCL) and Pseudomonas cepacia (LPS) lipases, suspended in organic solvents, were used to regioselectively acylate methyl 6-O-butyryl-alpha-D- and L-allopyranosides and methyl 6-O-butyryl-3-deoxy-alpha-D- and L-ribo-hexopyranosides. Both the D- and the L-3-deoxy sugars showed a complete regioselectivity, while the reactions of the allosides proved to be less regioselective. This indicates that the presence of the hydroxyl group at C-3 is an unfavourable factor for the action of the lipases.
Colombo
D
D
Dipartimento di Chimica e Biochimica Medica, Università di Milano, Italy.
Ronchetti
F
F
Scala
A
A
Taino
I M
IM
Toma
L
L
D000215:Acylation; D000818:Animals; D016956:Burkholderia cepacia / Q000201:enzymology; D002175:Candida / Q000201:enzymology; D006027:Glycosides / Q000737:chemistry* / Q000378:metabolism*; D006900:Hydroxylation; D066298:In Vitro Techniques; D008049:Lipase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010179:Pancreas / Q000201:enzymology; D013379:Substrate Specificity; D013552:Swine
D006027:Glycosides; D008049:Lipase