Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches.
An efficient synthesis of sialyllactosamine (SiaLacNAc) clusters using carbosilanes as core scaffolds has been accomplished by means of chemical and enzymatic approaches. N-Acetyl-D-glucosamine (GlcNAc) clusters having O-glycosidic linkage or S-glycosidic linkage were chemically synthesized from known intermediates in high yields. The GlcNAc clusters were first used as substrates for beta1,4 galactosyl transferase using UDP-galactose (UDP-Gal) as a sugar source to provide corresponding N-acetyllactosamine clusters. Further sugar elongation of the LacNAc clusters was demonstrated using alpha2,3 sialyl transferase and CMP-neuraminic acid (CMP-NANA) to yield the corresponding SiaLacNAc clusters.
Matsuoka
Koji
K
Area for Molecular Function, Division of Material Science, Graduate School of Science and Engineering, Saitama University, Sakura, Saitama 338-8570, Japan. koji@fms.saitama-u.ac.jp
Kaneko
Reina
R
Koyama
Tetsuo
T
Ma
XiaoTao
X
Esumi
Yasuaki
Y
Nakamura
Takemichi
T
Hatano
Ken
K
Terunuma
Daiyo
D
D000117:Acetylglucosamine / Q000096:biosynthesis / Q000737:chemistry; D000606:Amino Sugars / Q000096:biosynthesis / Q000737:chemistry* / Q000378:metabolism; D000818:Animals; D002240:Carbohydrate Sequence; D002417:Cattle; D009237:N-Acetyllactosamine Synthase / Q000378:metabolism; D051381:Rats; D012821:Silanes / Q000737:chemistry*; D014531:Uridine Diphosphate Galactose / Q000737:chemistry
D000606:Amino Sugars; D012821:Silanes; C504072:carbosilane; C032233:lactosamine; D014531:Uridine Diphosphate Galactose; C000458:N-acetyllactosamine; D009237:N-Acetyllactosamine Synthase; D000117:Acetylglucosamine