Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1996-11-27
2000-05-16
Lee, Howard C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, 536107, 536115, 536119, 435135, C08B 300, C08B 3102, C08B 3700
Patent
active
060639164
ABSTRACT:
Bacillus subtilis protease catalyzes the acylation of organic solvent-insoluble polysaccharides in isooctane solution containing vinyl esters of fatty acids as acyl donor. The reaction occurs only when the enzyme is solubilized via ion-pairing with the anionic surfactant dioctyl sulfosuccinate, sodium salt (AOT). Enzyme based acylation was demonstrated with amylose, cyclodextrins, cellulose, cellulose derivatives, and other polysaccharides such as chitosan, pullulan, and maltodextrose. These polysaccharides are reactive either as a cryogenically milled powder suspended in the organic solvent or as a thin film deposited onto ZnSe slides. For chitosan, .alpha.-cyclodextrin, and hydroxyethyl cellulose (HEC), the enzymatic crosslinking reaction occurs using adipic acid divinyl ester (C6DVE). HEC forms a compound that gels in solvents such as ethyl alcohol and dimethyl sulfone oxide (DMSO). Electron spectroscopy chemical analysis (ESCA) of the first 100 .ANG. of the amylose thin film amylose indicates that the acylated surface had a degree of substitution of 0.9.+-.0.1 acyl chains per glucose moiety and this corresponded well to the expected regioselectivity of subtilisin catalysis on glucose-containing compounds. .sup.1 H-NMR studies indicated that only the C-6 hydroxyl groups of the glucose moiety were acylated with amylose and .gamma.-cyclodextrin. However, .beta.-cyclodextrin, and .alpha.-cyclodextrin were modified at secondary alcohols and at all three alcohols, respectively. This approach represents the first attempt at using enzymes to modify organic solvent-insoluble polymers in nonaqueous media.
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Akkara Joseph A.
Bruno Ferdinando F.
Dordick Jonathan S.
Kaplan David L.
Lee Howard C.
Ranucci Vincent J.
The United States of America as represented by the Secretary of
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