Synthesis of N-linked pentasaccharides with isomeric glycosidic linkage.
As part of a program to explore the structural requirement of N-glycans in the carbohydrate-mediated biological interactions, N-linked pentasaccharide core structure was stereochemically modified in terms of glycosidic linkage. Three isomers, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-alpha-D-Man-(1-->4)-beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-L-Asn, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-beta-D-Man-(1-->4)-alpha-D-GlcNAc-(1-->4)-beta-D-GlcNAc-L-Asn, and alpha-D-Man-(1-->3)-[alpha-D-man-(1-->6)]-alpha-D-Man-(1-->4)-alpha-D-GlcNAc-(1-->4)-beta-D-GlcNAc-L-Asn, were synthesized. Synthesis of the pentasaccharide with natural linkage is also described.
Takatani
M
M
The Institute of Physical and Chemical Research (RIKEN), Wako-shi, Saitama, Japan.
Nakama
T
T
Kubo
K
K
Manabe
S
S
Nakahara
Y
Y
Ito
Y
Y
Nakahara
Y
Y
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D009844:Oligosaccharides; D011134:Polysaccharides