Chemoenzymatic synthesis of the sialyl-alpha-(2-->3')-lactosamine trisaccharide with a 3-aminopropyl group as a spacer at the reducing end.
The trisaccharide, 3-aminopropyl 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid-(2-->3)-beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside has been synthesized chemoenzymatically for the first time. First, the acceptor, 3-aminopropyl beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside was synthesized in a conventional chemical manner, and then it was coupled with CMP-sialic acid using alpha-(2-->3)-(N)-sialyltransferase to afford the desired trisaccharide by an enzymatically stereocontrolled manner.
Choudhury Mukherjee
Indrani
I
Laboratory of Advanced Bioelectronics, National Institute of Advanced Industrial Science and Technology (AIST), Central 5, 1-1-1 Higashi, Tsukuba, 305-8565, Ibaraki, Japan.
Minoura
Norihiko
N
Uzawa
Hirotaka
H
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004800:Enzymes, Immobilized / Q000737:chemistry / Q000378:metabolism; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012799:Sialyltransferases / Q000737:chemistry / Q000378:metabolism; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
C482410:3-aminopropyl-5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid-(2-3)-beta-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-beta-D-glucopyranoside; D004800:Enzymes, Immobilized; D005960:Glucosides; D009844:Oligosaccharides; D014312:Trisaccharides; C016735:sialooligosaccharides; D012799:Sialyltransferases