TY - JOUR
T1 - Synthesis of N-linked pentasaccharides with isomeric glycosidic linkage
AU - Takatani, Maki
AU - Nakama, Toshihiro
AU - Kubo, Kazusuke
AU - Manabe, Shino
AU - Nakahara, Yuko
AU - Ito, Yukishige
AU - Nakahara, Yoshiaki
PY - 2000/12/1
Y1 - 2000/12/1
N2 - 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, α-D-Man-(1→3)-[α-D-Man-(1→6)]-α -D-Man-(1→4)-β-D-GlcNAc-(1-→4)-β-D-GlcNAc-L-Asn, α-D-Man-(1→3)-[α-D-Man-(1→6)]-β -D-Man-(1→4)-α-D-GlcNAc-(1→4)-β-D-GlcNAc-L-Asn, and α-D-Man-(1→3)-[α-D-man-(1→6)]-α -D-Man-(1→4)-α-D-GlcNAc-(1→4)-β-D-GlcNAc-L-Asn, were synthesized. Synthesis of the pentasaccharide with natural linkage is also described.
AB - 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, α-D-Man-(1→3)-[α-D-Man-(1→6)]-α -D-Man-(1→4)-β-D-GlcNAc-(1-→4)-β-D-GlcNAc-L-Asn, α-D-Man-(1→3)-[α-D-Man-(1→6)]-β -D-Man-(1→4)-α-D-GlcNAc-(1→4)-β-D-GlcNAc-L-Asn, and α-D-Man-(1→3)-[α-D-man-(1→6)]-α -D-Man-(1→4)-α-D-GlcNAc-(1→4)-β-D-GlcNAc-L-Asn, were synthesized. Synthesis of the pentasaccharide with natural linkage is also described.
KW - N-glycan
KW - Synthesis
KW - Unnatural glycosidic linkage
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U2 - 10.1023/A:1007151913476
DO - 10.1023/A:1007151913476
M3 - Article
C2 - 11294502
AN - SCOPUS:0034465574
SN - 0282-0080
VL - 17
SP - 361
EP - 375
JO - Glycoconjugate Journal
JF - Glycoconjugate Journal
IS - 6
ER -