Efficient synthesis of glyceroyl beta-lactoside and its derivatives through a condensation reaction by cellulase.
Condensation reaction between lactose and glycerol was effectively catalyzed by utilizing a commercially available cellulase preparation from Trichoderma reesei. The enzyme induced the formation of 1-O-beta-lactosyl-(R,S)-glycerol (1) and 2-O-beta-lactosyl glycerol (2) in a molar ratio of 7:3 and in a 20% yield based on lactose added. The enzyme also induced the condensation of lactose with 1,3-propanediol to produce O-beta-lactosyl propanediol (3) in a yield of 15%. When various alkanols (N: 2-8) and allyl alcohol were used in the condensation reaction, the corresponding alkyl and allyl beta-lactoside were obtained in the yields of 0.9-3.8% of the desired compounds.
Yasutake
Nozomu
N
Science of Biological Resource, The United Graduate School of Agricultural Science, Gifu University, Yanagido 1-1, Japan.
Totani
Kazuhide
K
Harada
Yoichiro
Y
Haraguchi
Shinobu
S
Murata
Takeomi
T
Usui
Taichi
T
D002480:Cellulase / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D005990:Glycerol / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007785:Lactose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011409:Propylene Glycols / Q000737:chemistry; D011786:Quality Control; D014242:Trichoderma
D006027:Glycosides; D011409:Propylene Glycols; C008245:lactosides; C029976:4-aminophenyl beta-lactoside; C041787:1,3-propanediol; D002480:Cellulase; D007785:Lactose; D005990:Glycerol