Synthesis of glyceroyl beta-N-acetyllactosaminide and its derivatives through a condensation reaction by cellulase.
A condensation reaction between N-acetyllactosamine and glycerol was directly catalyzed by using a commercially available cellulase preparation from Trichoderma reesei. 1-O-beta-N-Acetyllactosaminyl-(R, S)-glycerols (1) were readily synthesized in a 5% yield based on the N-acetyllactosamine added and conveniently isolated by two-step column chromatographies. The use of a partially purified enzyme increased 2.3-fold the yield of 1, compared to that of the crude enzyme containing beta-D-galactosidase activity. When various alkanols (n:2-4) were used in the condensation reaction, the corresponding alkyl beta-N-acetyllactosaminides were obtained in yields of 0.3-1.1% of the desired compounds.
Yasutake
Nozomu
N
Science of Biological Resource, The United Graduate School of Agricultural Science, Gifu University, Japan.
Totani
Kazuhide
K
Harada
Yoichiro
Y
Haraguchi
Shinobu
S
Murata
Takeomi
T
Usui
Taichi
T
D002480:Cellulase / Q000378:metabolism*; D002852:Chromatography, Ion Exchange; D005990:Glycerol / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification; D007785:Lactose / Q000031:analogs & derivatives / Q000096:biosynthesis* / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D011786:Quality Control; D014242:Trichoderma / Q000201:enzymology
C485581:glyceroyl N-acetyllactosaminide; D002480:Cellulase; D007785:Lactose; D005990:Glycerol