Enzymatic synthesis of trehalose esters having lipophilicity.
To improve trehalose lipophilicity, trehalose was regioselectively esterified with vinyl fatty acid esters in dimethyl formamide by protease from Bacillus subtilis to give 6-O-lauroyltrehalose, 6-O-myristoyltrehalose, 6-O-palmitoyltrehalose, 6-O-stearoyltrehalose, 6-O-oleoyltrehalose and 6-O-linoleoyltrehalose. The influence of structural variation by changing fatty acid substitute was examined by measurement of the surface tension and biodegradability.
Raku
T
T
New Energy and Industrial Technology Development Organization (NEDO), Tsukuba Central 6, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8566, Japan.
Kitagawa
M
M
Shimakawa
H
H
Tokiwa
Y
Y
D001412:Bacillus subtilis / Q000737:chemistry / Q000201:enzymology; D001673:Biodegradation, Environmental; D004126:Dimethylformamide / Q000737:chemistry; D010450:Endopeptidases / Q000096:biosynthesis / Q000737:chemistry*; D004952:Esters; D005227:Fatty Acids / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry; D012988:Soil Microbiology; D013329:Structure-Activity Relationship; D013500:Surface Tension; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D014753:Vinyl Compounds / Q000737:chemistry
D004952:Esters; D005227:Fatty Acids; D008055:Lipids; D014753:Vinyl Compounds; D004126:Dimethylformamide; D014199:Trehalose; D010450:Endopeptidases