2-NAPHTHYL-BETA-D-GLUCOPYRANOSIDE Chemical Properties

Melting point:

183°C

Boiling point:

567.9±50.0 °C(Predicted)

Density 

1.454±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.80±0.70(Predicted)

2-NAPHTHYL-BETA-D-GLUCOPYRANOSIDE Usage And Synthesis

Uses

2-Naphthalenyl β-D-glucopyranoside is a synthetic sugar analogue that can be used in glycobiology research.

Definition

ChEBI: A beta-D-glucoside that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen is replaced by a 2-naphthyl group.

Synthesis

GENERAL STEPS: 30-50 μmol of 2-naphthol was dissolved in 0.5 mL of DMSO and diluted with buffer solution (50 mM Tris-HCl, pH 7.4, total volume 25 mL). Subsequently, 60-100 μmol of UDP-α-D-Glucose and 50 mL of AaGT3 crude enzyme solution extracted from wet-induced E. coli cells containing pET28a-AaGT3 were added. The reaction mixture was incubated at 30°C for no more than 12 hours. After completion of the reaction, five extractions were performed with 5 × 100 mL of ethyl acetate. The organic phases were combined and concentrated to dryness under reduced pressure. The residue was dissolved in 1.5 mL of methanol and purified by reversed-phase semi-preparative high-performance liquid chromatography (HPLC). The final product was structurally confirmed by mass spectrometry (MS) and nuclear magnetic resonance (NMR).

References

[1] Tetrahedron Letters, 2017, vol. 58, # 22, p. 2118 - 2121

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