A convergent synthesis of trisaccharides with alpha-Neu5Ac-(2 --> 3)-beta-D-gal-(1 --> 4)-beta-D-GlcNAc and alpha-Neu5Ac-(2 --> 3)-beta-D-gal-(1 --> 3)-alpha-D-GalNAc sequences.
The syntheses of three trisaccharides: alpha-Neu5Ac-(2 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-GlcNAc --> OMe, alpha-Neu5Ac-(2 --> 3)-beta-D-Gal6SO3Na-(1 --> 4)-beta-D-GlcNAc --> OMe, and alpha-Neu5Ac-(2 --> 3)-beta-D-Gal-(1 --> 3)-alpha-D-GalNAc --> OBn were accomplished by using either methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-beta-D-glycero-D-g alacto-2-nonulopyranoside)onate or methyl (phenyl N-acetyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-beta-D-gl ycero-D-galacto-2-nonulopyranoside)onate as the sialyl donor. The N,N-diacetylamino sialyl donor appears to be more reactive than its parent acetamido sugar when allowed to react with an disaccharide acceptor under the same glycosylation conditions. The trisaccharides, as well as the intermediate products, were fully characterized by 2D DQF 1H-1H COSY and 2D ROESY spectroscopy.
Xia
J
J
Molecular and Cellular Biophysics, Roswell Park Cancer Institute, Buffalo, NY 14263, USA.
Alderfer
J L
JL
Piskorz
C F
CF
Locke
R D
RD
Matta
K L
KL
D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008969:Molecular Sequence Data; D019158:N-Acetylneuraminic Acid / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D014312:Trisaccharides; C422167:benzyl ((5-acetamido--3,5--dideoxygalactonon-2-ulopyranosylonic acid)-2-3-galactopyranosyl)-(1-3)-2-acetamido-2-deoxygalactopyranoside; C422164:methyl ((5-acetamido--3,5-dideoxygalactonon-2-ulopyranosylonic acid)-(2-3)-6-O-sulfogalactopyranosyl)-(1-4)-2-acetamido-2-deoxyglucopyranoside; C422163:methyl ((5-acetamido-3,5-dideoxygalactonon-2-ulopyranosylonic acid)-2-3-galactopyranosyl)-(1-4)-2-acetamido-2-deoxyglucopyranoside; C076321:alpha-Neu5Ac-2-3-Gal-1-3-GlcNAc; D019158:N-Acetylneuraminic Acid