"Sweet silicones": biocatalytic reactions to form organosilicon carbohydrate macromers.
Immobilized lipase B from Candida antarctica (Novozyme 435) catalyzed the regioselective formation of ester bonds between organosilicon carboxylic diacids and a C1-O-alkylated sugar under mild reaction conditions (i.e., low temperature, neutral pH, solventless). Specifically, the acid-functionalized organosilicones reacted with the primary hydroxyl group at the C6 position of alpha,beta-ethyl glucoside during the regioselective esterification. The pure organosilicon-sugar conjugates were prepared in a one-step reaction without protection-deprotection steps and without activation of the acid groups with the integrity of the siloxane bonds. [reaction: see text]
Sahoo
Bishwabhusan
B
NSF IUCRC for Biocatalysis and Bioprocessing of Macromolecules, Othmer Department of Chemical and Biological Sciences and Engineering, Polytechnic University, Six Metrotech Center, Brooklyn, NY 11201, USA.
Brandstadt
Kurt F
KF
Lane
Thomas H
TH
Gross
Richard A
RA
D002175:Candida / Q000201:enzymology*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004800:Enzymes, Immobilized; D004951:Esterification; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D012828:Silicones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002241:Carbohydrates; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D012828:Silicones; C093667:Novozyme 435; D008049:Lipase