Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability.
To enhance water solubility of 10-undecylenic acid, which has anti-fungus, anti-bacterial and anti-virus activity, D-glucose, trehalose and sucrose were regioselectively esterified with vinyl 10-undecylenic acid ester in dimethyl formamide by a commercial protease, Bioprase conc., from Bacillus subtilis. 6-O-(10-Undecylenoyl) D-glucose, 6-O-(10-undecylenoyl) trehalose and 1'-O-(10-undecylenoyl) sucrose were obtained. The influence of structural variation by changing the sugar moiety was analyzed the surface tension and biodegradability.
Raku
Takao
T
New Energy and Industrial Technology Development Organization (NEDO), Tsukuba Central 6, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8566, Japan.
Kitagawa
Masaru
M
Shimakawa
Hiromi
H
Tokiwa
Yutaka
Y
D001412:Bacillus subtilis / Q000737:chemistry / Q000201:enzymology; D001673:Biodegradation, Environmental; D050260:Carbohydrate Metabolism; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry; D010450:Endopeptidases / Q000737:chemistry*; D004951:Esterification; D004952:Esters; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism; D012988:Soil Microbiology; D012995:Solubility; D013329:Structure-Activity Relationship; D013395:Sucrose / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism; D013500:Surface Tension; D014199:Trehalose / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism; D014476:Undecylenic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
D002241:Carbohydrates; D004952:Esters; D014476:Undecylenic Acids; D013395:Sucrose; D014199:Trehalose; D010450:Endopeptidases; D005947:Glucose