N-Acetyl-D-Glucosamine → beta-D-galactosyl-(1->4)-N-acetyl-D-glucosamine

HRID 1738774Notes

Reaction equation

HRID 1738774 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[OH:13][CH:14]1[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18](O)[C@H:16]([OH:17])[C@H:15]1[NH:24][C:25]([CH3:27])=[O:26]>>[O:1]([C@@H:18]1[C@@H:20]([CH2:22][OH:23])[O:21][CH:14]([OH:13])[C@H:15]([NH:24][C:25]([CH3:27])=[O:26])[C@H:16]1[OH:17])[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

3

Reactant 2

HCID 439174N-Acetyl-D-GlucosamineHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 9800166beta-D-galactosyl-(1->4)-N-acetyl-D-glucosamine

Procedure

The 1H-NMR spectrum of the difucosylated product (FIG. 3C, Table 3) showed that two fucoses had been transferred to the acceptor, yielding the glycan 4. The H-1 signals of the fucoses resonated at 5.117 ppm and 4.078(α)/5.091(β) ppm (3FucH-1 and 6FucH-1, respectively). In glycan 4 also the H-1 signals of 3Gal and 6Gal were shifted (-0.027 and -0.028 ppm, respectively) compared to the corresponding signals in glycan 3. In contrast, the H-1 signal of the branching galactose was practically unaffected, showing that the GlcNAc in the reducing end was not fucosylated. This confirms and extends previous data showing that branch forming Galβ1-4GlcNAc residues of polylactosamines are not fucosylated under the conditions used (Niemela et al., Glycoconjugate J. 12: 36-44 (1995)).

Sources & evidence

ORD record
ord-dab567116c51487ba0e4c0fba187e7ec
Source dataset
uspto-grants-1999_10
Patent number
US05965544

Reaction notes

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