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])O.C(=O)(O)[O-].[NH4+].[NH2:18]C1C=C(C(O)=O)C(O)=CC=1.C(Cl)(Cl)Cl>N1C=CC=CC=1.CO>[C@@H:11]1([NH2:18])[O:12][C@H:3]([CH2:2][OH:1])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@H:9]1[OH:10]Participants
Procedure
Beta-D-glucosylamine is prepared by the reaction of D-(+)-glucose with ammonium bicarbonate as described by Likhosherstov, L. M. et al. (Carbohydr. Res. 146: C1, 1986). A reaction mixture containing the glycosylamine and a 1- to 2-fold excess by weight of 5-aminosalicylic acid is allowed to react overnight in pyridine at 50° C. The reaction is monitored by thin-layer chromatography (TLC) (silica gel; eluent: CHCl3:MeOH, 1:1, by volume). The solvent is removed, and the reaction mixture is purified by chromatography on silica gel or BIOGEL-F2™ (BioRad, Richmond, Calif.), using absorbance at 254 nm as detection. The products are characterized by TLC on silica gel, electrospray mass spectrometry, and 1H- and 13C-NMR analysis. The transamination reaction is indicated by a downfield shift of resonance of the anomeric proton (observed at δ=4.1 ppm by analysis of the unsubstituted glycosyl-1-amine) to δ=4.3–4.7 ppm in the 1H-NMR spectrum of the β-anomer of the synthetic glycoconjugate product. (This anomer is the major product of the transamination reaction.)
Workup
- customThe solvent is removed
- customthe reaction mixture is purified by chromatography on silica gel or BIOGEL-F2™ (BioRad, Richmond, Calif.)
- customThe transamination reaction
- customthe major product of the transamination reaction
Sources & evidence
- ORD record
- ord-d32a83443cc04f33b3ec521ca4cfe7ab
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157444B2
Linked notes
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