2616-64-0

Basic information

• Product Name: (2S,3S,4R,5R,6R)-6-[[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-oxane-2-carboxylic
• Synonyms: (2S,3S,4R,5R,6R)-6-[[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-oxane-2-carboxylic;Uridine diphosphate glucuronic acid;UDP-D-glucuronic acid;UDP-glucuronic acid;Uridine 5'-(trihydrogen diphosphate)mono-α-D-glucopyranuronosyl;Uridine diphosphoglucuronic acid;Uridine pyrophosphoglucuronic acid;UDP-alpha-D-glucuronic acid
• CAS NO: 2616-64-0
• Molecular Formula: C₁₅H₂₂N₂O₁₈P₂
• Molecular Weight: 580.29
• Mol File: 2616-64-0.mol
• Article Data: 18

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.05g/cm³
• Refractive Index: 1.684
• PKA: 1.10±0.50(Predicted)
• CAS DataBase Reference: (2S,3S,4R,5R,6R)-6-[[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-oxane-2-carboxylic(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R,5R,6R)-6-[[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-oxane-2-carboxylic(2616-64-0)
• EPA Substance Registry System: (2S,3S,4R,5R,6R)-6-[[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-oxane-2-carboxylic(2616-64-0)

Safety Data

• Hazardous Substances Data: 2616-64-0(Hazardous Substances Data)

Usage

Description

An intermediate in the phase II reaction that results in the formation of glucuro_x0002_nic acid conjugates of xenobiotics which contain substituents such as hydroxyl, amino, or sulfhydryl groups, forming the O-, N-, and S-glucuronides, respectively. UDPGA is formed by two reactions: (i) the formation of UDPG from UTP and glucose 1-phosphate and (ii) the formation of UDPGA from UDPG. The two reactions are catalyzed by UDPG pyrophosphorylase and UDPG dehydrogenase, respectively, whereas glucuronide formation is catalyzed by glucuronosyltransferase. Glucuronide formation from xenobiotics is common in all animal groups except insects.

Definition

ChEBI: A UDP-sugar having alpha-D-glucuronic acid as the sugar component.

InChI:InChI=1/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1

Synthetic route

UDP (58-98-0) + Sucrose (57-50-1) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
With histidine-6-nicotinamide adenine dinucleotide hydride oxidase; histidine-6-uridine 5’-diphosphate-α-D-glucose-dehydrogenase; sucrose synthase 1; NAD In aq. buffer at 30℃; for 5h; pH=7.8; Enzymatic reaction;	100%
Multi-step reaction with 2 steps 1: sucrose synthase 1 / Enzymatic reaction 2: NAD; histidine-6-uridine 5’-diphosphate-α-D-glucose-dehydrogenase; histidine-6-nicotinamide adenine dinucleotide hydride oxidase / aq. buffer / 5 h / 30 °C / pH 8.7 / Enzymatic reaction View Scheme

D-glucuronic acid (70021-34-0) + UTP (63-39-8) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
With glucuronokinase from Arabidopsis thaliana; pyrophosphatase from E. coli; UDP-sugar pyrophosphorylasegene from Arabidopsis thaliana; ATP; magnesium chloride In aq. buffer at 37℃; pH=8; Enzymatic reaction;	89%

UDP-glucose (133-89-1) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
With Tris buffer; NAD; 2-oxo-propionic acid for 12h; lactate dehydrogenase, uridine 5'-diphosphoglucose dehydrogenase (UDP-Glc dehydrogenase);	87%
With UDP-glucose dehydrogenase; NAD; 2-oxo-propionic acid for 24h; Ambient temperature; pH 7.5 - 8.2;	68%
at 25℃; potassium bicinate buffer (pH 8.5), NAD(+), UDP-glucose dehydrogenase; kinetic parameters: Km, Vm;

D-glucuronic acid (6556-12-3, 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7) + UTP (63-39-8) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
With recombinant Arabidopsis thaliana glucuronokinase; molecular weight around 42 kDa; recombinant Bifidobacterium longum UDP-sugar pyrophosphorylase; recombinant Pasteurella multocida inorganic pyrophosphatase; ATP; magnesium chloride In aq. buffer at 37℃; for 36h; pH=6.5; Catalytic behavior; Reagent/catalyst; pH-value; Enzymatic reaction; chemoselective reaction;	80%
With glucuronokinase from Arabidopsis thaliana; inorganic pyrophosphatase from P. multocida; UDP-sugar pyrophosphorylase from Arabidopsis thaliana; ATP; sodium hydroxide; magnesium chloride In aq. buffer at 37℃; for 24h; pH=7.5; Enzymatic reaction;

O5'-(amino-hydroxy-phosphoryl)-uridine (15483-88-2) + α-D-glucopyranuronic acid 1-phosphate (6920-57-6, 7259-41-8, 10345-04-7, 13168-11-1, 46825-92-7, 58865-20-6, 69127-38-4) → UDP-glucuronic acid (2616-64-0)

uridine diphospho-α-D-gluco-hexodialdose (31932-92-0) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
With Streptococcus pyogenes UDP-glucose dehydrogenase; nicotinamide adenine dinucleotide Yield given;
With Streptococcus pyogenes UDP-glucose dehydrogenase; nicotinamide adenine dinucleotide Rate constant; Michaelis constant;

O5'-<2-α-D-glucopyranosyloxy-1,2-dihydroxy-diphosphoryl>-uridine → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
enzymatische Synthese mit Hilfe von UDPglucose-dehydrogenase aus Leber-Homogenaten;
enzymatische Synthese mit Hilfe von UDPglucose-dehydrogenase aus Knorpel-Homogenaten;
enzymatische Synthese mit Hilfe von UDPglucose-dehydrogenase aus Erbsen-Saemlingen;
enzymatische Synthese mit Hilfe von UDPglucose-dehydrogenase aus Extrakten von Pneumococcus-Staemmen;

α-D-glucopyranuronic acid 1-phosphate (6920-57-6, 7259-41-8, 10345-04-7, 13168-11-1, 46825-92-7, 58865-20-6, 69127-38-4) + UTP → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
reversible enzymatische Bildung mit Hilfe eines Enzym-Praeparats aus Phaseolus aureus;

Acetic acid (2S,3R,4S,5S,6S)-2,3,5-triacetoxy-6-formyl-tetrahydro-pyran-4-yl ester (61259-51-6) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: Zn, TiCl4 2: H3PO4 / 50 °C 3: NaOMe / methanol 4: 1.) O3, 2.) Me2S / 1.) -78 deg C, 2.) -20 deg C, 12 h 5: UDP-glucose pyrophosphorylase, pyrophosphotase 6: Streptococcus pyogenes UDP-glucose dehydrogenase, NAD(+) / Michaelis constant View Scheme

UTP (63-39-8) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: UDP-glucose pyrophosphorylase, pyrophosphotase 2: Streptococcus pyogenes UDP-glucose dehydrogenase, NAD(+) / Michaelis constant View Scheme
Multi-step reaction with 2 steps 1: Bacillus cerius UDP-Glc phosphorylase / Enzymatic reaction 2: recombinant Bacillus cerius UDP-glucose 6-dehydrogenase; nicotinamide adenine dinucleotide / 0.25 h / 37 °C / pH 8 / aq. phosphate buffer; Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: bovine serum albumin; magnesium chloride; S. cerevisiae hexokinase; rabbit muscle phosphoglucomutase; UTP-glucose-1-phosphate uridylyltransferase from Bifidobacterium longum subsp. longum JCM 1217; S. cerevisiae inorganic pyrophosphatase; 6-phospho-α-D-glucopyranosyl-1-phosphate / aq. buffer / 24 h / 30 °C / pH 7.5 / Enzymatic reaction 2: 9,10-phenanthrenequinone; Candida tenuis xylose reductase; nicotinamide adenine dinucleotide; human UDP-glucose dehydrogenase; dihydrogen peroxide / aq. buffer / 3 h / 37 °C / pH 7.5 / Enzymatic reaction View Scheme

Phosphoric acid mono-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-vinyl-tetrahydro-pyran-2-yl) ester (194541-55-4) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) O3, 2.) Me2S / 1.) -78 deg C, 2.) -20 deg C, 12 h 2: UDP-glucose pyrophosphorylase, pyrophosphotase 3: Streptococcus pyogenes UDP-glucose dehydrogenase, NAD(+) / Michaelis constant View Scheme

Phosphoric acid mono-((2R,3R,4S,5S,6S)-6-formyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yl) ester (38183-89-0) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: UDP-glucose pyrophosphorylase, pyrophosphotase 2: Streptococcus pyogenes UDP-glucose dehydrogenase, NAD(+) / Michaelis constant View Scheme

Acetic acid (2S,3R,4S,5R,6R)-2,3,5-triacetoxy-6-vinyl-tetrahydro-pyran-4-yl ester (194541-54-3) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: H3PO4 / 50 °C 2: NaOMe / methanol 3: 1.) O3, 2.) Me2S / 1.) -78 deg C, 2.) -20 deg C, 12 h 4: UDP-glucose pyrophosphorylase, pyrophosphotase 5: Streptococcus pyogenes UDP-glucose dehydrogenase, NAD(+) / Michaelis constant View Scheme

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-phosphonooxy-6-vinyl-tetrahydro-pyran-3-yl ester → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOMe / methanol 2: 1.) O3, 2.) Me2S / 1.) -78 deg C, 2.) -20 deg C, 12 h 3: UDP-glucose pyrophosphorylase, pyrophosphotase 4: Streptococcus pyogenes UDP-glucose dehydrogenase, NAD(+) / Michaelis constant View Scheme

1,2,3,4-tetra-O-acetyl-β-D-glucopyranose (13100-46-4) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 7 steps 1: DMSO, CMC, Cl2CHCO2H 2: Zn, TiCl4 3: H3PO4 / 50 °C 4: NaOMe / methanol 5: 1.) O3, 2.) Me2S / 1.) -78 deg C, 2.) -20 deg C, 12 h 6: UDP-glucose pyrophosphorylase, pyrophosphotase 7: Streptococcus pyogenes UDP-glucose dehydrogenase, NAD(+) / Michaelis constant View Scheme

cytidine-5'-phosphoro-(2-aminoimidazole) (69673-09-2) → UDP-glucuronic acid (2616-64-0)

Conditions

Yield

Multi-step reaction with 4 steps 1: 1) Tri n-butylammonium pyrophosphate, 2) NaClO4 / 1) AcCN, 1 d; 2) acetone, diethyl ether 2: 95 percent / NaNO2 / acetic acid; H2O / 48 h / 4 °C 3: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 4: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme

uridine 5’-monophosphate-imidazole (56428-57-0) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) Tri n-butylammonium pyrophosphate, 2) NaClO4 / 1) AcCN, 1 d; 2) acetone, diethyl ether 2: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 3: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme

Phosphoric acid mono-[(2R,3S,4R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester; compound with tributyl-amine (51450-21-6) → UDP-glucuronic acid (2616-64-0)

Conditions

Yield

Multi-step reaction with 5 steps 1: acetonitrile / 24 h / 25 °C 2: 1) Tri n-butylammonium pyrophosphate, 2) NaClO4 / 1) AcCN, 1 d; 2) acetone, diethyl ether 3: 95 percent / NaNO2 / acetic acid; H2O / 48 h / 4 °C 4: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 5: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme

Trioctyl-amine; compound with phosphoric acid mono-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester (62540-53-8) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: acetonitrile / 24 h / 25 °C 2: 1) Tri n-butylammonium pyrophosphate, 2) NaClO4 / 1) AcCN, 1 d; 2) acetone, diethyl ether 3: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 4: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme

Cytidine 5'-triphosphate (54619-78-2) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / NaNO2 / acetic acid; H2O / 48 h / 4 °C 2: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 3: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme

uridine 5'-triphosphate sodium salt (19817-92-6) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 2: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme

cytidine monophosphate (63-37-6) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: ethanol; methanol / 1 h / Heating 2: acetonitrile / 24 h / 25 °C 3: 1) Tri n-butylammonium pyrophosphate, 2) NaClO4 / 1) AcCN, 1 d; 2) acetone, diethyl ether 4: 95 percent / NaNO2 / acetic acid; H2O / 48 h / 4 °C 5: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 6: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme
Multi-step reaction with 4 steps 1: enzymatically at pH 7.5-7.8 2: 95 percent / NaNO2 / acetic acid; H2O / 48 h / 4 °C 3: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 4: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme

5'-Uridylic Acid (58-97-9) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: ethanol; methanol / 1 h / Heating 2: acetonitrile / 24 h / 25 °C 3: 1) Tri n-butylammonium pyrophosphate, 2) NaClO4 / 1) AcCN, 1 d; 2) acetone, diethyl ether 4: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 5: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme
Multi-step reaction with 3 steps 1: enzymatically at pH 7.6 2: uridine-5'-diphosphoglucose pyrophosphorylase, inorganic pyrophosphatase / enzymatically at pH 7.6 3: 68 percent / UDP-glucose dehydrogenase, NAD+, pyruvate, L-LDH / 24 h / Ambient temperature; pH 7.5 - 8.2 View Scheme

uridine 5'-diphospho-D-galactose (2956-16-3) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
With NAD In dimethyl sulfoxide at 30℃; for 0.25h; pH=8.7; Enzyme kinetics;

uridine 5'-diphosphoglucose disodium salt (6858-46-4, 7333-33-7, 14656-80-5, 28053-08-9, 53829-41-7, 108320-88-3, 137868-52-1) → UDP-glucuronic acid (2616-64-0)

Conditions	Yield
With human UDP-glucose 6-dehydrogenase wild-type; sodium β-nicotinamide adenine dinucleotide phosphate In water-d2 at 25℃; for 16h; Mechanism; pH-value; Solvent; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction;

D-Glucose (2280-44-6) → UDP-glucuronic acid (2616-64-0)

Conditions

Yield

Multi-step reaction with 2 steps 1: bovine serum albumin; magnesium chloride; S. cerevisiae hexokinase; rabbit muscle phosphoglucomutase; UTP-glucose-1-phosphate uridylyltransferase from Bifidobacterium longum subsp. longum JCM 1217; S. cerevisiae inorganic pyrophosphatase; 6-phospho-α-D-glucopyranosyl-1-phosphate / aq. buffer / 24 h / 30 °C / pH 7.5 / Enzymatic reaction 2: 9,10-phenanthrenequinone; Candida tenuis xylose reductase; nicotinamide adenine dinucleotide; human UDP-glucose dehydrogenase; dihydrogen peroxide / aq. buffer / 3 h / 37 °C / pH 7.5 / Enzymatic reaction View Scheme

homovanillyl alcohol (2380-78-1) + UDP-glucuronic acid (2616-64-0) → 2-[3′-hydroxy-4′-(β-D-glucopyranosyluronic acid)phenyl]ethanol + homovanillic alcohol 1-O-β-D-glucuronide

Conditions	Yield
With Tris-HCl buffer; calcium chloride; diothiothreitol; benzenesulfonamide; uridine 5'-diphosphoglucuronyl transferases (porcine liver) In water; dimethyl sulfoxide at 35℃; for 6h; pH=8.0; Enzymatic reaction;	A 88% B 6.1%

Magnolol (528-43-8) + UDP-glucuronic acid (2616-64-0) → Magnolol glucuronide (102141-20-8)

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	79%

morin (480-16-0) + UDP-glucuronic acid (2616-64-0) → morin-7-O-β-D-glucuronide

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	78%

19-nortestosterone (434-22-0) + UDP-glucuronic acid (2616-64-0) → 17β-hydroxyestr-4-en-3-one 17-O-glucuronide (131749-24-1) + 3α-hydroxy-5α-estran-17-one glucuronide (294213-86-8) + 3α-hydroxy-5β-estran-17-one glucuronide

Conditions	Yield
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4;	A 77% B n/a C n/a

7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) + UDP-glucuronic acid (2616-64-0) → 4-methylumbelliferyl-β-D-glucuronide (6160-80-1)

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	75%
With rat liver microsome solution; magnesium chloride In various solvent(s) at 37℃; for 0.166667h; pH=7.4;

3,7,3',4'-tetrahydroxyflavone (528-48-3) + UDP-glucuronic acid (2616-64-0) → Fisetin 7-O-glucuronide

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	68%

diosmetin (520-34-3) + UDP-glucuronic acid (2616-64-0) → diosmentin-7-O-β-D-glucuronopyranoside (35110-20-4)

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	67%

6-{2-[(1-methylethyl)amino]propyl}pyridin-3-ol (76906-79-1, 78152-30-4, 78152-32-6) + UDP-glucuronic acid (2616-64-0) → 2-{2-[(1-methylethyl)amino]propyl}pyridin-5-yl β-D-glucopyranosiduronic acid

Conditions	Yield
With guinea-pig liver preparation; HEPES buffer; magnesium chloride at 37℃; for 118h; pH=7.4; glucuronidation;	63.9%

UDP-glucuronic acid (2616-64-0) + (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) → (-)-epicatechin-7-O-β-D-glucuronide

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	61%

5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on (491-80-5) + UDP-glucuronic acid (2616-64-0) → 7-(β-D-glucopyranuronosyloxy)-5-hydroxy-4'-methoxyisoflavone

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	61%

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2) + UDP-glucuronic acid (2616-64-0) → phloretin-2′-O-β-D-glucuronide (123685-24-5) + phloretin-4′-O-β-D-glucuronide

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	A 9% B 58%

kaempferol (520-18-3) + UDP-glucuronic acid (2616-64-0) → kaempferol-7-O-β-D-glucuronide (249938-52-1)

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	57%

3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + UDP-glucuronic acid (2616-64-0) → 3-(4'-hydroxyphenyl)propanol 4'-O-β-D-glucuronide + 3-(4'-hydroxyphenyl)propanol 1-O-β-D-glucuronide

Conditions	Yield
With Tris-HCl buffer; calcium chloride; diothiothreitol; benzenesulfonamide; uridine 5'-diphosphoglucuronyl transferases (porcine liver) In water; dimethyl sulfoxide at 35℃; for 8h; pH=8.0; Enzymatic reaction;	A 56% B 5.5%

UDP-glucuronic acid (2616-64-0) + taxifolin (480-18-2) → (2R,3R)-dihydroquercetin-7-O-β-D-glucuronide

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	50%

UDP-glucuronic acid (2616-64-0) + hesperetin (520-33-2) → Hesperetin 7-O-glucuronide

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; pH=7; Kinetics; Reagent/catalyst; Solvent; pH-value; Temperature; Enzymatic reaction;	50%

p-hydroxyphenethyl alcohol (501-94-0) + UDP-glucuronic acid (2616-64-0) → 4-(2-hydroxyethyl)phenyl β-D-glucopyranosiduronic acid + tyrosol 1-O-β-D-glucuronide

Conditions	Yield
With Tris-HCl buffer; calcium chloride; diothiothreitol; benzenesulfonamide; uridine 5'-diphosphoglucuronyl transferases (porcine liver) In water; dimethyl sulfoxide at 35℃; for 8h; pH=8.0; Enzymatic reaction;	A 41.7% B 5.4%

formoterol (128954-45-0) + UDP-glucuronic acid (2616-64-0) → 2-(formylamino)-4-(1-hydroxy-2-{[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)phenyl β-D-glucopyranosiduronic acid

Conditions	Yield
With guinea-pig liver preparation; HEPES buffer; magnesium chloride at 37℃; for 118h; pH=7.4; glucuronidation;	37%

hydroxytyrosol (10597-60-1) + UDP-glucuronic acid (2616-64-0) → (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxy-4-(2-hydroxyethyl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid + 2-[4′-hydroxy-3′-(β-D-glucopyranosyluronic acid)phenyl]ethanol

Conditions	Yield
With Tris-HCl buffer; calcium chloride; diothiothreitol; benzenesulfonamide; uridine 5'-diphosphoglucuronyl transferases (porcine liver) In water; dimethyl sulfoxide at 35℃; for 8h; pH=8.0; Enzymatic reaction;	A 36.1% B 15.4%

5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) + UDP-glucuronic acid (2616-64-0) → Chrysin glucuronide (35775-49-6)

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	36%

17β-hydroxy-1-methyl-5α-androst-1-en-3-one (153-00-4) + UDP-glucuronic acid (2616-64-0) → 1-methyl-5α-androst-1-1en-3-one-17β-O-glucuronide + 3α-hydroxy-1-methylen-5α-androstan-17-one glucuronide

Conditions	Yield
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4;	A 24% B 28%

metandienone (72-63-9) + UDP-glucuronic acid (2616-64-0) → 17β-methyl-5β-androst-1-ene-17α-ol-3α-O-glucuronide (1062581-61-6) + 17α-methyl-5β-androstane-17β-ol-3α-O-glucuronide

Conditions	Yield
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4;	A 25% B n/a

oxachelin + UDP-glucuronic acid (2616-64-0) → 23-O-β-D-glucopyranosyloxachelin

Conditions	Yield
With OleD Loki glycosyltransferase(P67T/I112P/T113M/S132F/A242I); magnesium chloride In aq. buffer at 25℃; pH=8; Enzymatic reaction;	24%

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone (518-82-1) + UDP-glucuronic acid (2616-64-0) → emodin-3-O-β-D-glucuronide

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	24%

(R)-2-(2-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydrooxazole (1337978-34-3) + UDP-glucuronic acid (2616-64-0) → 2-O-β-D-glucopyranosylspoxazomicin C + 12-O-β-D-glucopyranosylspoxazomicin C

Conditions	Yield
With OleD Loki glycosyltransferase(P67T/I112P/T113M/S132F/A242I); magnesium chloride In aq. buffer at 25℃; pH=8; Enzymatic reaction;	A 20% B 10%

N-salicyloyl-2-aminopropane-1,3-diol + UDP-glucuronic acid (2616-64-0) → N-(6-O-β-D-glucopyranosyl)salicyloyl-2-aminopropane-1,3-diol

Conditions	Yield
With OleD Loki glycosyltransferase(P67T/I112P/T113M/S132F/A242I); magnesium chloride In aq. buffer at 25℃; pH=8; Enzymatic reaction;	19%

testosterone (58-22-0) + UDP-glucuronic acid (2616-64-0) → Androstane-3,17-diol Glucuronide (95237-44-8)

Conditions	Yield
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4;	16%

Upstream product

• 15483-88-2 O^5'-(amino-hydroxy-phosphoryl)-uridine 
• 6920-57-6 α-D-glucopyranuronic acid 1-phosphate 
• 58-98-0 UDP 
• 57-50-1 Sucrose 
• 2280-44-6 D-Glucose 
• 133-89-1 UDP-glucose 
• 6294-16-2 D-galacturonic acid 
• 63-39-8 UTP 
• 489-91-8 D-galacturonic acid 
• 59-56-3 α-D-glucopyranosyl-1-phosphate 
• 70021-34-0 D-glucuronic acid 
• 6556-12-3 D-glucuronic acid 
• 6858-46-4 uridine 5'-diphosphoglucose disodium salt 
• 2956-16-3 uridine 5'-diphospho-D-galactose 

Downstream Products

• 3616-06-6 UDP-xylose 
• 17680-99-8 4-Methylphenol glucuronide 
• 19132-91-3 4-Hydroxybiphenyl glucuronide 
• 17681-00-4 4-Chlorophenol glucuronide 
• 26910-19-0 4-Methoxyphenol glucuronide 
• 10344-94-2 p-nitrophenyl-β-D-glucuronide 
• 6160-80-1 4-methylumbelliferyl-β-D-glucuronide 
• 29741-09-1 apigenin-7-O-β-D-glucuronide 
• 29741-07-9 5,4'-dihydroxy-3'-methoxyflavone-7-O-β-galacturonide 
• 1106675-29-9 C₂₇H₂₉O₁₈⁽¹⁺⁾ 
• 1106675-24-4 C₂₇H₂₉O₁₈⁽¹⁺⁾ 
• 1106675-30-2 C₂₇H₂₉O₁₈⁽¹⁺⁾ 
• 1106675-28-8 C₂₇H₂₉O₁₈⁽¹⁺⁾ 
• 1106675-21-1 C₂₇H₂₉O₁₇⁽¹⁺⁾ 

Relevant articles and documents

Identification of novel inhibitors of UDP-Glc 4′-epimerase, a validated drug target for african sleeping sickness

Novel inhibitors of Trypanosoma brucei and mammalian UDP-Glc 4′-epimerase were identified by screening a small library of natural products and commercially available drug-like molecules. The inhibitors possess low micromolar potency against the T. brucei and human enzymes in vitro, display a degree of selectivity between the two enzymes, and are cytotoxic to cultured T. brucei and mammalian cells.

Enzymatic Synthesis of Uridine 5'-Diphosphoglucuronic Acid on a Gram Scale

A pratical route to uridine 5'-diphosphoglucuronic acid (UDP-GlcUA) from uridine 5'-diphosphoglucose (UDP-Glc) on a 1-g scale has been developed using uridine 5'-diphosphoglucose dehydrogenase (UDP-Glc DH, EC 1.1.1.22) from bovine liver.Crude UDP-Glc dehydrogenase was isolated fron beef liver (450 units from 2.4 kg of frozen liver).Commercially available UDP-Glc dehydrogenase as well as a preparation fron calf liver acetone powder were also evaluated as catalysts for large-scale production of UDP-GlcUA: both preparations exhibited too little activity to be synthetically useful.A platinum-catalyzed oxygen oxidation of UDP-Glc was also examined as a possible route to UDP-GlcUA: enzymatic oxidation was superior.These results establish a route to another of the important activated monosaccharides required for cell-free enzymatic syntheses of mammalian oligo- and polysaccharides.

Catalytic mechanism of human UDP-glucose 6-dehydrogenase: In situ proton NMR studies reveal that the C-5 hydrogen of UDP-glucose is not exchanged with bulk water during the enzymatic reaction

Human UDP-glucose 6-dehydrogenase (hUGDH) catalyzes the biosynthetic oxidation of UDP-glucose into UDP-glucuronic acid. The catalytic reaction proceeds in two NAD+-dependent steps via covalent thiohemiacetal and thioester enzyme intermediates. Formation of the thiohemiacetal adduct occurs through attack of Cys276 on C-6 of the UDP-gluco-hexodialdose produced in the first oxidation step. Because previous studies of the related enzyme from bovine liver had suggested loss of the C-5 hydrogen from UDP-gluco-hexodialdose due to keto-enol tautomerism, we examined incorporation of solvent deuterium into product(s) of UDP-glucose oxidation by hUGDH. We used wild-type enzyme and a slow-reacting Glu161→Gln mutant that accumulates the thioester adduct at steady state. In situ proton NMR measurements showed that UDP-glucuronic acid was the sole detectable product of both enzymatic transformations. The product contained no deuterium at C-5 within the detection limit (≤2%). The results are consistent with the proposed mechanistic idea for hUGDH that incipient UDP-gluco-hexodialdose is immediately trapped by thiohemiacetal adduct formation.

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Uridine diphosphate beta-glucuronic acid. A new substrate for beta-glucuronidase.

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Gram-scale production of sugar nucleotides and their derivatives

Here, we report a practical sugar nucleotide production strategy that combined a high-concentrated multi-enzyme catalyzed reaction and a robust chromatography-free selective precipitation purification process. Twelve sugar nucleotides were synthesized on a gram scale with a purity up to 98%.

Isotope Probing of the UDP-Apiose/UDP-Xylose Synthase Reaction: Evidence of a Mechanism via a Coupled Oxidation and Aldol Cleavage

The C-branched sugar d-apiose (Api) is essential for plant cell-wall development. An enzyme-catalyzed decarboxylation/pyranoside ring-contraction reaction leads from UDP-α-d-glucuronic acid (UDP-GlcA) to the Api precursor UDP-α-d-apiose (UDP-Api). We examined the mechanism of UDP-Api/UDP-α-d-xylose synthase (UAXS) with site-selectively2H-labeled and deoxygenated substrates. The analogue UDP-2-deoxy-GlcA, which prevents C-2/C-3 aldol cleavage as the plausible initiating step of pyranoside-to-furanoside conversion, did not give the corresponding Api product. Kinetic isotope effects (KIEs) support an UAXS mechanism in which substrate oxidation by enzyme-NAD+and retro-aldol sugar ring-opening occur coupled in a single rate-limiting step leading to decarboxylation. Rearrangement and ring-contracting aldol addition in an open-chain intermediate then give the UDP-Api aldehyde, which is intercepted via reduction by enzyme-NADH.