ChemicalBook CAS DataBase List UDP-D-galactose

UDP-D-galactose synthesis

7synthesis methods

Product Name:UDP-D-galactose
CAS Number:2956-16-3
Molecular formula:C15H24N2O17P2
Molecular Weight:566.3

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63-39-8 Synthesis

63-39-8
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2956-16-3
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Yield:2956-16-3 86%

Reaction Conditions:

with Pasteurella multocida inorganic pyrophosphatase;Bifidobacterium longumuridine 5'-diphosphate-sugarpyrophosphorylase;Echerichia coli galactokinase;adenosine-5'-triphosphate;magnesium chloride in aq. buffer at 37; pH=8; for 24 h;Enzymatic reaction;Reagent/catalyst;

Steps:

4 Uridine 5′-diphospho-α-D-galactopyranoside (UDP-Gal, T6-16)

Monosaccharides and derivatives (30-100 mg, 1.0 eq.), ATP (1.2 eq.), and UTP (1.3 eq.) were dissolved in water in a 15 mL centrifuge tube containing Tris-HCl buffer (100 mM, pH 8.0) and MgCl₂(10 mM). After the addition of appropriate amount of NahK_ATCC15697, EcGalK, or SpGalK (1.3-4.5 mg), BLUSP (1.0-2.5 mg), and PmPpA (1.5-2.5 mg), millipore water was added to bring the total volume of the reaction mixture to 10 mL. The reaction was carried out by incubating the solution in an isotherm incubator for 24 hr at 37° C. with gentle shaking or without shaking. In the synthesis of UDP-Glc, commercially available Glc-1-P (55.2 mg), UTP (1.2 eq.), Tris-HCl buffer (100 mM, pH 8.0), and MgCl₂(10 mM) were used along with BLUSP (1 mg) and PmPpA (1.5 mg). The reaction was left for 2 hr at 37° C. in isotherm with gentle shaking. Product formation was monitored by TLC (EtOAc:MeOH:H₂O:AcOH=5:3:3:0.3 by volume) with p-anisaldehyde sugar staining. The reaction was terminated by adding the same volume of ice-cold ethanol and incubating at 4° C. for 30 min followed by centrifugation remove the enzymes. The supernatant was collected and concentrated and passed through a BioGel P-2 gel filtration column to afford the product. Silica gel column purification (EtOAc:MeOH:H₂O=7:3:2) was applied when necessary to achieve further purification.135 mg. Yield, 86%; white foam. ¹H NMR (600 MHz, D₂O) δ 7.93 (d, J=8.4 Hz, 1H), 5.97-5.95 (m, 2H), 5.63 (dd, J=7.2, 3.6 Hz, 1H), 4.37-4.35 (m, 2H), 4.28-4.18 (m, 3H), 4.16 (t, J=6 Hz, 1H), 4.02 (d, J=3 Hz, 1H), 3.90 (dd, J=10.2, 3.6 Hz, 1H), 3.80 (dt, J=10.2, 3.3 Hz, 1H), 3.76-3.71 (m, 2H). ¹³C NMR (150 MHz, D₂O) δ 166.39, 151.96, 141.78, 102.80, 96.01 (d, J=6.6 Hz), 88.65, 83.32 (d, J=8.9 Hz), 73.93, 72.11, 69.78, 69.43, 69.24, 68.50 (d, J=7.8 Hz), 65.15 (d, J=5.0 Hz), 61.16. HRMS (ESI) m/z calcd for C₁₅H₂₄N₂O₁₇P₂(M-H) 565.0472, found 565.0453.