Enzymatic synthesis of two salicin analogues by reaction of salicyl alcohol with Bacillus macerans cyclomaltodextrin glucanyltransferase and Leuconostoc mesenteroides B-742CB dextransucrase.
Beta-Salicin is a naturally occurring glycoside found in the bark of poplar and willow trees. Ancient man used it as an analgesic and antipyretic. It has a D-glucopyranose unit attached by a beta-linkage to the phenolic hydroxyl of salicyl alcohol. Two new salicin analogues have been enzymatically synthesized by transglycosylation reactions: (a) by the reaction of Bacillus macerans cyclomaltodextrin glucanyltransferase with cyclomaltohexaose and salicyl alcohol, followed by reactions with alpha amylase and glucoamylase to give D-glucopyranose attached by an alpha-linkage to the phenolic hydroxyl of salicyl alcohol as the major product, alpha-salicin; and (b) by the reaction of Leuconostoc mesenteroides B-742CB dextransucrase with sucrose and salicyl alcohol, followed by reactions with dextranase and glucoamylase to give alpha-d-glucopyranose attached to the primary alcohol hydroxyl of salicyl alcohol as the major product, alpha-isosalicin.
Yoon
Seung-Heon
SH
Laboratory of Carbohydrate Chemistry and Enzymology, Iowa State University, Ames, IA 50011, USA.
Bruce Fulton
D
D
Robyt
John F
JF
D001407:Bacillus / Q000201:enzymology*; D001592:Benzyl Alcohols / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D005087:Glucan 1,4-alpha-Glucosidase / Q000378:metabolism; D005960:Glucosides; D005964:Glucosyltransferases / Q000378:metabolism*; D007934:Leuconostoc / Q000201:enzymology*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D008970:Molecular Weight; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013395:Sucrose / Q000378:metabolism; D000516:alpha-Amylases / Q000378:metabolism
D001592:Benzyl Alcohols; D005960:Glucosides; C005696:salicin; D013395:Sucrose; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase; C020025:dextransucrase; D000516:alpha-Amylases; D005087:Glucan 1,4-alpha-Glucosidase; C010631:salicyl alcohol