63-39-8

Basic information

• Product Name: UTP
• Synonyms: 5'-URIDYLATE TRIPHOSPHATE;UTP;UTP, 3NA;UTP-NA;UTP, NA3H;UTP SODIUM SALT;UTP TRISODIUM SALT;URIDINE 5'-TRIPHOSPHATE
• CAS NO: 63-39-8
• Molecular Formula: C₉H₁₅N₂O₁₅P₃
• Molecular Weight: 484.14
• EINECS: 243-347-5
• Mol File: 63-39-8.mol
• Article Data: 18

Chemical Properties

• Flash Point: 113 °C
• Appearance: /
• Density: 2.106 g/cm³
• Storage Temp.: −20°C
• PKA: pK1:7.58 (25°C)
• CAS DataBase Reference: UTP(CAS DataBase Reference)
• NIST Chemistry Reference: UTP(63-39-8)
• EPA Substance Registry System: UTP(63-39-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-68/20/21/22
• Safety Statements: 22-26-36
• WGK Germany: 1
• Hazardous Substances Data: 63-39-8(Hazardous Substances Data)

Usage

Description

Uridine triphosphate (UTP;Uridine 5'-triphosphate) is a nucleotide that regulates the functions of the pancreas in endocrine and exocrine secretion, proliferation, channels, transporters, and intracellular signaling under normal and disease states.

Occurrence

Uridine 5'-triphosphate is a natural product found in Helianthus tuberosus, Apis cerana, and other organisms with data available.

Uses

Uridine 5′-triphosphate trisodium salt solution has been used to increase the intracellular Ca2+ levels in rat primary tracheal epithelial cells. It has also been used as a nucleotide substrate to analyze the activity of MutT homologue 1 (MTH1).

Definition

UTP is a pyrimidine ribonucleoside 5'-triphosphate having uracil as the nucleobase. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a pyrimidine ribonucleoside 5'-triphosphate and a uridine 5'-phosphate. It is a conjugate acid of an UTP(4-) and an UTP(3-).

Biochem/physiol Actions

P2Y receptor agonist

Pharmacokinetics

INS316 is a short-acting, aerosolized uridine 5-triphosphate (UTP) solution used as a diagnostic aid for lung cancer. INS316 appears to improve sputum expectoration mediated through the P2Y2 receptor, a nucleotide receptor expressed in human airway epithelial cells and some other tissues. UTP binding to the P2Y2 receptor triggers signal transduction that leads to chloride ion secretion, thereby resulting in mucociliary clearance of airway.

in vitro

Uridine triphosphate treatment induces Schwannoma cell migration through activation of P2Y2 receptors and through the increase of extracellular matrix metalloproteinase-2 (MMP-2) activation and expression. Uridine triphosphate-induced proliferation is mediated by protein kinase D, Src-family tyrosine kinase, Ca/calmodulin-dependent protein kinase II, phosphatidylinositol 3-kinase (PI3K), Akt, and phospholipase D. Uridine triphosphate increases phosphorylation of Akt through protein kinase C, Src-family tyrosine kinase, Ca/calmodulin-dependent protein kinase II, and PI3K.

in vivo

Uridine triphosphate reduces mitochondrial calcium levels following hypoxia. Early or late uridine triphosphate preconditioning is effective to reduce infarct size and superior myocardial function. Uridine triphosphate treatment increases the number of monocytes and macrophages infiltrating the pouch and up-regulates the gene expression of IL-4 and IL-13 in the regional lymph nodes.

References

[1]. Lamarca A, et al. Uridine 5'-triphosphate promotes in vitro Schwannoma cell migration through matrix metalloproteinase-2 activation. PLoS One. 2014 Jun 6;9(6):e98998.[2]. Choi JH, et al. Uridine triphosphate increases proliferation of human cancerous pancreatic duct epithelial cells by activating P2Y2 receptor. Pancreas. 2013 May;42(4):680-6.[3]. Yitzhaki S, et al. Uridine-5'-triphosphate (UTP) reduces infarct size and improves rat heart function aftermyocardial infarct. Biochem Pharmacol. 2006 Oct 16;72(8):949-55.[4]. Iwaki Y, et al. Enhancement of antibody production against rabies virus by uridine 5'-triphosphate in mice. Microbes Infect. 2014 Mar;16(3):196-202.

Synthetic route

5'-Uridylic Acid (58-97-9) → UDP (58-98-0) + UTP (63-39-8)

Conditions	Yield
With N-ethylmorpholine buffer; phosphorotriimidazolide at 22℃; for 72h; other 5'-nucleotides, also with phosphorotribenzimidazolide, MnCl2; other time, temperature;	A 25% B 36%
With phosphorotriimidazolide; magnesium chloride at 22℃; for 72h; N-ethylmorpholine buffer (pH 7.0);	A 25% B 36%

C9H14N2O16P4 → UTP (63-39-8)

Conditions	Yield
With pyridine; water; iodine In N,N-dimethyl-formamide at 20℃; for 2.25h;	9.3%

orotic acid (65-86-1) → UTP (63-39-8)

Conditions	Yield
durch Biosynthese;

5'-Uridylic Acid (58-97-9) + ATP (56-65-5) → UTP (63-39-8)

Conditions	Yield
reversible enzymatische Bildung mit Hilfe von wss. Nucleosidmonophosphat-kinase aus Hefe-Praeparaten;
reversible enzymatische Bildung mit Hilfe von wss. Nucleosidmonophosphat-kinase aus Leber-Praeparaten;
reversible enzymatische Bildung mit Hilfe von wss. Nucleosidmonophosphat-kinase aus Erbsen-Samen;

uridine 5'-(2-deoxy-α-D-glucopyranosyl diphosphate) (13491-28-6, 13529-36-7, 28196-62-5, 65309-82-2, 18521-38-5) → 2-deoxy-α-D-glucopyranosyl (42400-47-5) + UTP (63-39-8)

Conditions	Yield
With sodium pyrophosphate; uridine-5'-diphosphoglucose pyrophosohorylase; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride; bovine serum albumin In water at 25℃; for 72h;

uridine-5'-diphosphoglucose (952585-00-1) → glucose 1-phosphate (59-56-3, 2240-08-6, 2255-14-3, 2520-52-7, 6799-01-5, 10456-01-6, 14048-34-1, 15978-07-1, 19993-19-2, 20299-62-1, 40591-51-3, 62057-78-7, 77280-79-6, 78341-19-2) + UTP (63-39-8)

Conditions	Yield
With UDPG pyrophosphorylase In water at 25℃; for 4h; Equilibrium constant; pH 7.2;

UDP (58-98-0) → UTP (63-39-8)

Conditions	Yield
With polyphosphate; Escherichia coli polyphosphate kinase; tris hydrochloride In water at 37℃; for 16h;	49.6 % Chromat.
With rabbit muscle pyruvate kinase; potassium chloride; phosphoenolpyruvic acid; D,L-dithiothreitol at 20℃; pH=7.5; Kinetics; Concentration; Reagent/catalyst; Tris buffer;

O5'-<2-α-D-glucopyranosyl-1,2-dihydroxy-diphosphoryl>-uridine → UTP (63-39-8)

Conditions	Yield
With pyrophosphoric acid mit Hilfe von Glucose-1-phosphat-uridylyltransferase;

O5'--O2',O3'-isopropyliden-uridine + tetramethylammonium salt of diphosphoric acid-tribenzyl ester → UTP (63-39-8)

Conditions	Yield
With acetonitrile anschl. mit m-Kresol und anschl. Hydrieren an Palladium/Kohle in wss. Aethanol und Behandeln mit wss. LiOH;

phosphoenolpyruvic acid (138-08-9) + UDP → UTP (63-39-8)

Conditions	Yield
durch enzymatische Bildung mit Hilfe von Pyruvatkinase aus Kaninchenmuskelgewebe;

ATP (56-65-5) + UDP → UTP (63-39-8)

Conditions	Yield
reversible enzymatische Bildung mit Hilfe von wss. Nucleosiddiphosphat-kinase aus Hefe-Praeparaten und tierischen Gewebeextrakten;
reversible enzymatische Bildung mit Hilfe von wss. Nucleosiddiphosphat-kinase aus Erbsen-Samen;

yeast RNA → guanosine 5'-triphosphate (86-01-1) + cytidine triphosphate (65-47-4) + UTP (63-39-8) + ATP (56-65-5)

Conditions	Yield
With sodium hydroxide; potassium phosphate; nuclease P1; PAN-immobilized PNPase; phospho(enol)pyruvic acid mono potassium salt; magnesium chloride; manganese(ll) chloride 1.) water, 50 deg C, 1 h, 2.) room temperature, 4 days; Yield given. Multistep reaction. Yields of byproduct given;

ribonucleic acid → UTP (63-39-8) + other nucleotides

Conditions	Yield
With magnesium oxide at 140 - 145℃; in wss. Loesung (pH 8 -8.5) und Behandeln des Nucleosid-Gemisches in wss. Loesung (pH ca. 7) in Gegenwart von Hefe und Dextrose mit NaH2PO4 und Na2HPO4;

5'-Uridylic Acid (58-97-9) + dicyclohexyl-carbodiimide (538-75-0) → UTP (63-39-8) + UDP

Conditions	Yield
With pyridine; tributyl-amine; phosphoric acid
With pyridine; phosphoric acid

C14H22N3O8P → UTP (63-39-8)

Conditions	Yield
With tris(tetra-n-butylammonium) hydrogen pyrophosphate In tetrahydrofuran at 20℃; for 0.5h;	45 mg

2',3'-O-(methoxymethylidene)uridine (16628-81-2) → UTP (63-39-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 690 mg / N-methylimidazole; pyridine / tetrahydrofuran / 20 °C 2: LiHMDS / tetrahydrofuran / 2 h / -78 - 0 °C 3: 215 mg / aq. HCl / acetonitrile / 4 h / 20 °C / pH 2.0 4: H2 / Pd/C / tetrahydrofuran / 2 h / 20 °C 5: 45 mg / tris(tetra-n-butylammonium) hydrogen pyrophosphate / tetrahydrofuran / 0.5 h / 20 °C View Scheme

(4-Chloro-butyl)-methyl-phosphoramidic acid benzyl ester (3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester → UTP (63-39-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 215 mg / aq. HCl / acetonitrile / 4 h / 20 °C / pH 2.0 2: H2 / Pd/C / tetrahydrofuran / 2 h / 20 °C 3: 45 mg / tris(tetra-n-butylammonium) hydrogen pyrophosphate / tetrahydrofuran / 0.5 h / 20 °C View Scheme

5'-uridyl benzyl N-methyl-N-(4-chlorobutyl)phosphoramidate (727398-81-4) → UTP (63-39-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd/C / tetrahydrofuran / 2 h / 20 °C 2: 45 mg / tris(tetra-n-butylammonium) hydrogen pyrophosphate / tetrahydrofuran / 0.5 h / 20 °C View Scheme

(4-Chloro-butyl)-methyl-phosphoramidic acid benzotriazol-1-yl ester (3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (727399-01-1) → UTP (63-39-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: LiHMDS / tetrahydrofuran / 2 h / -78 - 0 °C 2: 215 mg / aq. HCl / acetonitrile / 4 h / 20 °C / pH 2.0 3: H2 / Pd/C / tetrahydrofuran / 2 h / 20 °C 4: 45 mg / tris(tetra-n-butylammonium) hydrogen pyrophosphate / tetrahydrofuran / 0.5 h / 20 °C View Scheme

2',3'-O-isopropylideneuridine (362-43-6) → UTP (63-39-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; chlorophosphoric acid dibenzyl ester / -40 - -30 °C / anschl. Hydrierung 2: aqueous H3PO4; aqueous pyridine View Scheme

C9H11Cl2N2O7P → 5'-Uridylic Acid (58-97-9) + UTP (63-39-8)

Conditions	Yield
With tributyl-amine; bis(tri-n-butylammonium) pyrophosphate In N,N-dimethyl-formamide at -15℃; for 2h;	A n/a B 107 mg

uridine (58-96-8) → 5'-Uridylic Acid (58-97-9) + UTP (63-39-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate / trimethyl phosphite / 2 h / -15 °C 2: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate / N,N-dimethyl-formamide / 2 h / -15 °C View Scheme

uridine 5'-diphospho-N-acetylglucosamine (528-04-1, 2616-63-9, 7277-98-7, 16465-33-1, 19014-00-7, 26234-54-8, 26575-17-7, 27963-82-2, 29217-44-5, 125639-14-7) → UTP (63-39-8)

Conditions	Yield
With pyrophosphate tetraanion; recombinant Arabidopsis N-acetylglucosamine-1-phosphate uridylyltransferase-1; magnesium chloride at 37℃; for 0.166667h; pH=7.6; Kinetics; Concentration; Reagent/catalyst; aq. buffer; Enzymatic reaction;

uridine-5'-diphospho-N-acetyl-D-galactosamine (528-04-1, 2616-63-9, 7277-98-7, 16465-33-1, 19014-00-7, 26234-54-8, 26575-17-7, 27963-82-2, 29217-44-5, 125639-14-7) → N-acetylgalactosamine-1-phosphate + UTP (63-39-8)

Conditions	Yield
With pyrophosphate tetraanion; recombinant Arabidopsis N-acetylglucosamine-1-phosphate uridylyltransferase-1; magnesium chloride at 37℃; for 0.166667h; pH=7.6; Kinetics; Reagent/catalyst; Concentration; aq. buffer; Enzymatic reaction;

uridine (58-96-8) → UTP (63-39-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere 2: pyridine; iodine; water / N,N-dimethyl-formamide / 2.25 h / 20 °C View Scheme

UTP (63-39-8) + α-D-glucopyranosyl-1-phosphate (59-56-3) → UDP-glucose (133-89-1)

Conditions	Yield
With Pasteurella multocida inorganic pyrophosphatase; Bifidobacterium longumuridine 5'-diphosphate-sugarpyrophosphorylase; adenosine-5'-triphosphate; magnesium chloride In aq. buffer at 37℃; for 2h; pH=8; Enzymatic reaction;	99%
With Glucose-1-phosphate thymidylyltransferase from Streptococcus pneumonia serotype 23F; magnesium chloride at 37℃; for 1h; Enzymatic reaction;	94%
With GalU; α(1->3) galactotransferase; α(1->4) galactotransferase; manganese(ll) chloride at 37℃; for 48h; pH=7; Inert atmosphere; aq. buffer; Enzymatic reaction;	70%

N-azidoacetylgalactosamine + UTP (63-39-8) → 5’-diphospho-2-azidoacetamido galactosamine

Conditions	Yield
With recombinant human GalNAc kinase GK2; recombinant human UDP-GalNAc pyrophosphorylase AGX1; ATP; yeast inorganic pyrophosphatase In various solvent(s) at 37℃; pH=8.8;	99%

glucose 1-phosphate (59-56-3, 2240-08-6, 2255-14-3, 2520-52-7, 6799-01-5, 10456-01-6, 14048-34-1, 15978-07-1, 19993-19-2, 20299-62-1, 40591-51-3, 62057-78-7, 77280-79-6, 78341-19-2) + UTP (63-39-8) → UDP-glucose (133-89-1)

Conditions	Yield
With recombinant Bifidobacterium longum ATCC55813 UDP-sugar pyrophosphorylase; recombinant Pasteurella multocida P-1059 inorganic pyrophosphatase; magnesium chloride at 37℃; for 2h; pH=8; aq. buffer; Enzymatic reaction;	99%
With yeast inorganic pyrophosphatase; recombinant Arabidopsis N-acetylglucosamine-1-phosphate uridylyltransferase-2; magnesium chloride at 37℃; for 0.166667h; pH=7.6; aq. buffer; Enzymatic reaction;

N-acetylglucosamine-1-phosphate (28446-21-1) + UTP (63-39-8) → uridine 5'-diphospho-N-acetylglucosamine (528-04-1, 2616-63-9, 7277-98-7, 16465-33-1, 19014-00-7, 26234-54-8, 26575-17-7, 27963-82-2, 29217-44-5, 125639-14-7)

Conditions	Yield
With yeast inorganic pyrophosphatase; N-acetylglucosamine-1-phosphate pyrophosphorylase from C. jejuni NCTC 11168; tris hydrochloride; magnesium chloride at 37℃; for 2h; pH=7.5;	97.9%
With Pyrococcus furiosus enzyme; magnesium(II) In various solvent(s) at 80℃; pH=7.5; Enzyme kinetics;
With Pyrococcus furious enzyme; magnesium(II) In various solvent(s) at 80℃; for 1h; pH=7.5;

2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose (667462-08-0) + UTP (63-39-8) → uridine 5'-diphospho-2-deoxy-2-trifluoroacetamido-α-D-glucopyranoside (212137-54-7)

Conditions	Yield
With inorganic pyrophosphatase cloned from Pasteurella multocida strain P-1059; N-acetylglucosamine-1-phosphate uridylyltransferase cloned from Pasteurella multocida strain P-1059 (ATCC15742); N-acetylhexosamine 1-kinase cloned from Bifidobacterium longum ATCC55813; ATP; magnesium chloride In water at 37℃; pH=8; aq. buffer; Enzymatic reaction;	97%
With hydrogenchloride; N-acetylglucosamine-1-phosphate uridylyltransferase from Escherichia coli K12 MG1655; pyrophosphatase from Escherichia coli K12 MG1655; recombinant N-acetylhexosamine 1-kinase; ATP; magnesium chloride In aq. buffer at 37℃; pH=8.5; Concentration; Temperature; pH-value; Enzymatic reaction;
With inorganic pyrophosphatase from P. multocida; N-acetyl hexosamine 1-kinase from Bifidobacterium infantis; UDP-N-acetylgalactosamine pyrophosphorylase from Pasteurella multocida; ATP; sodium hydroxide; magnesium chloride In aq. buffer at 37℃; for 24h; pH=7; Enzymatic reaction;

ammonium 2-acetamido-2,6-dideoxy-6-fluoro-α-D-glucopyranosyl-1-phosphate + UTP (63-39-8) → uridine 5'-diphospho-2-acetamido-2,6-dideoxy-6-fluoro-α-D-glucopyranose diammonium salt

Conditions	Yield
With pyrophosphatase from C. cerevisiae; uridyl transferase GlmU from E. coli K12; magnesium chloride In aq. buffer at 37℃; for 24h; pH=7.5; Enzymatic reaction;	95%

ammonium 2-acetamido-2,6-dideoxy-6-thio-α-D-glucopyranosyl-1-phosphate + UTP (63-39-8) → uridine 5'-diphospho-2-acetamido-2,6-dideoxy-6-thio-α-D-glucopyranose diammonium salt

Conditions	Yield
With pyrophosphatase from C. cerevisiae; uridyl transferase GlmU from E. coli K12; magnesium chloride; D,L-dithiothreitol In aq. buffer at 37℃; for 24h; pH=7.5; Enzymatic reaction;	93%

2-deoxy-2-fluoro-D-mannopyranoside (7226-39-3, 7241-17-0, 28876-44-0, 38711-37-4, 55449-80-4, 62182-10-9, 62182-14-3, 86783-82-6, 98856-44-1, 98856-45-2, 98856-46-3, 31077-88-0) + UTP (63-39-8) → uridine 5'-diphospho-2-fluoro-2-deoxy-α-D-mannopyranoside (67341-44-0)

Conditions	Yield
With recombinant Bifidobacterium infantis ATCC15697 N-acetylhexosamine 1-kinase; recombinant Bifidobacterium longum ATCC55813 UDP-sugar pyrophosphorylase; recombinant Pasteurella multocida P-1059 inorganic pyrophosphatase; ATP; magnesium chloride at 37℃; for 24h; pH=8; aq. buffer; Enzymatic reaction;	92%

2-deoxy-2-trifluoroacetamido-5-thio-D-glucose + UTP (63-39-8) → C17H24F3N3O16P2S

Conditions	Yield
With ATP; magnesium chloride In aq. buffer at 37℃; for 36h;	92%

UTP (63-39-8) + α-D-galactose-1-phosphate (59-56-3, 2240-08-6, 2255-14-3, 2520-52-7, 6799-01-5, 10456-01-6, 14048-34-1, 15978-07-1, 19993-19-2, 20299-62-1, 40591-51-3, 62057-78-7, 77280-79-6, 78341-19-2) → uridine 5'-diphospho-D-galactose (2956-16-3)

Conditions	Yield
With inorganic pyrophosphatase; recombinant thymidylyltransferase from Aneurinibacillus thermoaerophilus DSM 10155; magnesium chloride at 55℃; for 1.5h; pH=7.5; Inert atmosphere; aq. buffer; Enzymatic reaction;	90%
With Glucose-1-phosphate thymidylyltransferase from Streptococcus pneumonia serotype 23F for 48h; Enzymatic reaction;	86%
With phosphate buffer; UDPG-PPase from Pyrococcus furiosus DSM 3638 at 90℃; pH=7.5; Enzyme kinetics;

2-azido-2-deoxy-D-mannopyranose (97604-58-5) + UTP (63-39-8) → uridine 5'-diphospho-2-azido-2-deoxy-α-D-mannopyranoside (1363386-22-4)

Conditions	Yield
With recombinant Bifidobacterium infantis ATCC15697 N-acetylhexosamine 1-kinase; recombinant Bifidobacterium longum ATCC55813 UDP-sugar pyrophosphorylase; recombinant Pasteurella multocida P-1059 inorganic pyrophosphatase; ATP; magnesium chloride at 37℃; for 24h; pH=8; aq. buffer; Enzymatic reaction;	90%

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%

D-Galactose (10257-28-0) + UTP (63-39-8) → uridine 5'-diphospho-D-galactose (2956-16-3)

Conditions	Yield
With recombinant Bifidobacterium longum ATCC55813 UDP-sugar pyrophosphorylase; recombinant Escherichia coli K-12 galactokinase; recombinant Pasteurella multocida P-1059 inorganic pyrophosphatase; ATP; magnesium chloride at 37℃; for 24h; pH=8; aq. buffer; Enzymatic reaction;	86%
With Pasteurella multocida inorganic pyrophosphatase; Bifidobacterium longumuridine 5'-diphosphate-sugarpyrophosphorylase; Echerichia coli galactokinase; adenosine-5'-triphosphate; magnesium chloride In aq. buffer at 37℃; for 24h; pH=8; Reagent/catalyst; Enzymatic reaction;	86%
With pyrophosphatase; Streptococcus pneumoniae TIGR4 galactokinase; Arabidopsis thaliana uridine-diphosphate-sugar pyrophosphorylase; ATP; magnesium chloride In aq. buffer at 42℃; for 1h; pH=8; Enzymatic reaction;
With galactokinase from Bifidobacterium infantis; 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;

ammonium 2-acetamido-2,6-dideoxy-α-D-glucopyranosyl-1-phosphate + UTP (63-39-8) → uridine 5'-diphospho-2-acetamido-2,6-dideoxy-α-D-glucopyranose diammonium salt

Conditions	Yield
With pyrophosphatase from C. cerevisiae; uridyl transferase GlmU from E. coli K12; magnesium chloride In aq. buffer at 37℃; for 24h; pH=7.5; Enzymatic reaction;	86%

C8H14NO9P(2-)*2Na(1+) + UTP (63-39-8) → P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt (91183-98-1)

Conditions	Yield
With 1,4-dithio-D,L-threitol; magnesium chloride at 30℃; for 3h; pH=7; aq. buffer; Enzymatic reaction;	85%

ammonium 2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranosyl-1-phosphate + UTP (63-39-8) → uridine 5'-diphospho-2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranose diammonium salt

Conditions	Yield
With pyrophosphatase from C. cerevisiae; uridyl transferase GlmU from E. coli K12; magnesium chloride In aq. buffer at 37℃; for 48h; pH=7.5; Enzymatic reaction;	84%

N-acetyl-D-galactosamine (72-87-7, 1136-42-1, 1136-44-3, 6730-06-9, 7772-94-3, 10036-64-3, 14131-60-3, 14131-64-7, 14131-68-1, 14215-68-0, 62057-49-2, 62057-50-5, 62057-51-6, 62057-52-7, 62057-53-8, 62057-54-9, 62057-55-0, 62057-56-1, 62075-50-7, 62137-54-6, 134451-97-1, 134522-12-6, 148347-16-4, 6082-29-7) + UTP (63-39-8) → uridine 5'-diphospho-2-acetamido-2-deoxy-α-D-glacopyranoside (1146981-86-3)

Conditions	Yield
With Pasteurella multocida inorganic pyrophosphatase; Pasteurella multocida N-acetylglucosamine-1-phosphate uridylyltransferase; adenosine-5'-triphosphate; MTESNEVLFGIASHFALEGAVTGIEPYGDGHINTTYLVTTDGPRYILQQMNTSIFPDTVNLMRNVELVTSTLKAQGKETLDIVPTTSGATWAEIDGGAWRVYKFIEHTMSYNLVPNPDVFREAGSAFGDFQNFLSEFDASQLTETIAHFHDTPHRFEDFKAALAADKLGRAAACCPEIDFYLSHADQYAVVMDGLRDGSIPLRVTHNDTKLNNILMDATTGKARAIIDLDTIMPGSMLFDFGDSIRFGASTALEDERDLSKVHFSTELFRAYTEGFVGELRGSITAREAELLPFSGNLLTMECGMRFLADYLEGDIYFATKYPEHNLVRTRTQIKLVQEMEQKASETHAIVADIMEAARLE; magnesium chloride In water at 37℃; for 24h; pH=8; Enzymatic reaction;	83%
With recombinant human GalNAc kinase GK2; recombinant human UDP-GalNAc pyrophosphorylase AGX1; ATP; yeast inorganic pyrophosphatase In various solvent(s) at 37℃; for 6h; pH=8.8;	68%
With pyrophosphatase; N-acetylhexosamine kinase; GalNAc pyrophosphorylase; ATP In aq. buffer at 37℃; pH=7.5; Enzymatic reaction;
With Bifidobacterium longum subsp. longum N-acetylhexosamine 1-kinase; Escherichia coli N-acetylglucosamine 1-phosphate uridyltransferase; ATP; sodium hydroxide; magnesium chloride In aq. buffer at 37℃; for 7h; pH=8.5; Inert atmosphere; Enzymatic reaction;

N-Acetyl-D-glucosamine (7512-17-6, 72-87-7, 1136-42-1, 1136-44-3, 6082-29-7, 6730-06-9, 7772-94-3, 10036-64-3, 14131-60-3, 14131-64-7, 14131-68-1, 14215-68-0, 62057-49-2, 62057-50-5, 62057-51-6, 62057-52-7, 62057-53-8, 62057-54-9, 62057-55-0, 62057-56-1, 62075-50-7, 62137-54-6, 134451-97-1, 134522-12-6, 148347-16-4) + UTP (63-39-8) → uridine 5'-diphospho-N-acetylglucosamine (528-04-1, 2616-63-9, 7277-98-7, 16465-33-1, 19014-00-7, 26234-54-8, 26575-17-7, 27963-82-2, 29217-44-5, 125639-14-7)

Conditions	Yield
With inorganic pyrophosphatase cloned from Pasteurella multocida strain P-1059; N-acetylglucosamine-1-phosphate uridylyltransferase cloned from Pasteurella multocida strain P-1059 (ATCC15742); N-acetylhexosamine 1-kinase cloned from Bifidobacterium longum ATCC55813; ATP; magnesium chloride In water at 37℃; pH=8; aq. buffer; Enzymatic reaction;	81%
With Pasteurella multocida inorganic pyrophosphatase; Pasteurella multocida N-acetylglucosamine-1-phosphate uridylyltransferase; adenosine-5'-triphosphate; MTESNEVLFGIASHFALEGAVTGIEPYGDGHINTTYLVTTDGPRYILQQMNTSIFPDTVNLMRNVELVTSTLKAQGKETLDIVPTTSGATWAEIDGGAWRVYKFIEHTMSYNLVPNPDVFREAGSAFGDFQNFLSEFDASQLTETIAHFHDTPHRFEDFKAALAADKLGRAAACCPEIDFYLSHADQYAVVMDGLRDGSIPLRVTHNDTKLNNILMDATTGKARAIIDLDTIMPGSMLFDFGDSIRFGASTALEDERDLSKVHFSTELFRAYTEGFVGELRGSITAREAELLPFSGNLLTMECGMRFLADYLEGDIYFATKYPEHNLVRTRTQIKLVQEMEQKASETHAIVADIMEAARLE; magnesium chloride In aq. buffer at 37℃; Enzymatic reaction;	81%
With inorganic pyrophosphatase; glucose-1-phosphate thymidylyltransferase from Aneurinibacillus thermoaerophilus DSM10155; N-acetylhexosamine kinase from Bifidobacterium longum; ATP; magnesium chloride In aq. buffer at 37 - 55℃; for 4h; pH=7.5; Enzymatic reaction;
With hydrogenchloride; N-acetylglucosamine-1-phosphate uridylyltransferase from Escherichia coli K12 MG1655; pyrophosphatase from Escherichia coli K12 MG1655; recombinant N-acetylhexosamine 1-kinase; ATP; magnesium chloride In aq. buffer at 37℃; pH=8.5; Concentration; Temperature; pH-value; Enzymatic reaction;
With inorganic pyrophosphatase from P. multocida; N-acetyl hexosamine 1-kinase from Bifidobacterium infantis; UDP-N-acetylgalactosamine pyrophosphorylase from Pasteurella multocida; ATP; sodium hydroxide; magnesium chloride In aq. buffer at 37℃; for 24h; pH=7.5; Enzymatic reaction;

UTP (63-39-8) → 5-Iodo-UTP (34198-43-1, 73202-51-4, 80160-19-6)

Conditions	Yield
With N-iodo-succinimide; sodium azide In water for 15h; regioselective reaction;	80%
With N-iodo-succinimide; sodium azide In water at 60℃; for 15h; regioselective reaction;	79%

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;

2-deoxy-2-propionylamido-α-D-glucopyranosyl phosphate + UTP (63-39-8) → uridine-5'-(2-deoxy-2-propionylamido-α-D-glucopyranosyl diphosphate)

Conditions	Yield
With yeast inorganic pyrophosphatase; N-acetylglucosamine-1-phosphate pyrophosphorylase from C. jejuni NCTC 11168; tris hydrochloride; magnesium chloride at 37℃; for 2h; pH=7.5;	79.9%

UTP (63-39-8) + mannose-1-phosphate (59-56-3, 2240-08-6, 2255-14-3, 2520-52-7, 6799-01-5, 10456-01-6, 14048-34-1, 15978-07-1, 19993-19-2, 20299-62-1, 40591-51-3, 62057-78-7, 77280-79-6, 78341-19-2) → Uridine diphosphate mannose (133-89-1, 2956-16-3, 7307-71-3, 7349-77-1, 16375-64-7, 16375-65-8, 16414-46-3, 17012-87-2, 25318-68-7, 78391-94-3, 99020-05-0, 99945-86-5)

Conditions	Yield
With Glucose-1-phosphate thymidylyltransferase from Streptococcus pneumonia serotype 23F for 48h; Enzymatic reaction;	78%
With phosphate buffer; UDPG-PPase from Pyrococcus furiosus DSM 3638 at 90℃; pH=7.5; Enzyme kinetics;
With phosphate buffer; UDPG-PPase from Pyrococcus furiosus DSM 3638; magnesium chloride at 90℃; for 0.5h;	92 % Turnov.

D-Galactose (10257-28-0) + UTP (63-39-8) → uridine-5'-diphosphogalactose (133-89-1, 2956-16-3, 7307-71-3, 7349-77-1, 16375-64-7, 16375-65-8, 16414-46-3, 17012-87-2, 25318-68-7, 78391-94-3, 99020-05-0, 99945-86-5)

Conditions	Yield
With galactokinase; pyruvate kinase; inorganic pyrophosphatase; phosphoenolpyruvic acid; galactose-1-phosphate uridylyltransferase; GalU; ATP; uridine-5'-diphosphoglucose at 30℃; for 24h; pH=8; aq. phosphate buffer; Inert atmosphere;	78%
With inorganic pyrophosphatase; galactokinase from Meiothermus taiwanensis; UDP-sugar pyrophosphorylase pyrophosphorylase from Arabidopsis thaliana; ATP; magnesium chloride In aq. buffer at 42℃; for 1h; pH=9; Enzymatic reaction;

2-Deoxy-2-[(trifluoroacetyl)amino]-D-glucopyranose-1-(dihydrogen phosphate) disodium salt + UTP (63-39-8) → P'-[2-deoxy-2-[(2,2,2-trifluoroacetyl)amino]-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt

Conditions	Yield
With 1,4-dithio-D,L-threitol; magnesium chloride at 30℃; for 3h; pH=7; aq. buffer; Enzymatic reaction;	78%

adenosine 5'-phosphorimidazolide (20816-58-4, 116273-87-1) + UTP (63-39-8) → P1-5'-O-adenosine-P4-5'-O-uridine tetraphosphate

Conditions	Yield
With H96F-Fhit; magnesium chloride In various solvent(s) at 20℃; for 1h; pH=5.5;	73%

UTP (63-39-8) + 2-acetamido-6-azido-2,6-dideoxy-D-glucopyranoside → uridine 5'-diphospho-2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranoside (1202854-85-0)

Conditions	Yield
With inorganic pyrophosphatase cloned from Pasteurella multocida strain P-1059; N-acetylglucosamine-1-phosphate uridylyltransferase cloned from Pasteurella multocida strain P-1059 (ATCC15742); N-acetylhexosamine 1-kinase cloned from Bifidobacterium longum ATCC55813; ATP; magnesium chloride In water at 37℃; pH=8; aq. buffer; Enzymatic reaction;	72%

UDP-glucose (133-89-1) + C6H13O8P (1375486-69-3) + UTP (63-39-8) → uridine-5'-diphospho-5-deoxy-D-galactofuranose (1346254-09-8)

Conditions	Yield
With inorganic pyrophosphatase; UDP-glucose pyrophosphorylase; galactose-1-phosphate uridyltransferase	71%

2-butyramido-2-deoxy-α-D-glucopyranosyl phosphate (884856-17-1) + UTP (63-39-8) → uridine-5'-(2-butyramido-2-deoxy-α-D-glucopyranosyl diphosphate)

Conditions	Yield
With yeast inorganic pyrophosphatase; N-acetylglucosamine-1-phosphate pyrophosphorylase from C. jejuni NCTC 11168; tris hydrochloride; magnesium chloride at 37℃; for 2h; pH=7.5;	70.6%

UDP-glucose (133-89-1) + UTP (63-39-8) + 6-deoxy-α-D-galactofuranosyl phosphate → uridine-5'-diphospho-6-deoxy-D-galactofuranose (1000874-38-3)

Conditions	Yield
With inorganic pyrophosphatase; UDP-glucose pyrophosphorylase; galactose-1-phosphate uridyltransferase	70%

C8H14NO9P(2-)*2Na(1+) + UTP (63-39-8) → P'-[2-(acetylamino)-2-deoxy-α-D-galactopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt (108320-87-2)

Conditions	Yield
With 1,4-dithio-D,L-threitol; magnesium chloride at 30℃; for 48h; pH=7; aq. buffer; Enzymatic reaction;	70%

Upstream product

• 13491-28-6 uridine 5'-(2-deoxy-α-D-glucopyranosyl diphosphate) 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 58-97-9 5'-Uridylic Acid 
• 538-75-0 dicyclohexyl-carbodiimide 
• 58-96-8 uridine 
• 67-48-1 choline chloride 
• 65-86-1 orotic acid 
• 4105-38-8 Tri-O-acetyluridine 
• 4105-38-8 2',3',5'-tri-O-acetyl-uridine 
• 82913-19-7 [(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate 
• 58-96-8 uridine 
• 528-04-1 uridine-5'-diphospho-N-acetyl-D-galactosamine 
• 528-04-1 uridine 5'-diphospho-N-acetylglucosamine 
• 362-43-6 2',3'-O-isopropylideneuridine 

Downstream Products

• 133-89-1 UDP-glucose 
• 65-47-4 cytidine triphosphate 
• 58-98-0 UDP 
• 10527-48-7 P¹-5'-O-adenosine-P⁴-5'-O-uridine tetraphosphate 
• 528-04-1 uridine 5'-diphospho-N-acetylglucosamine 
• 38168-82-0 glyceric acid 1,3-biphosphate 
• 1245697-26-0 UDP-glucuronic acid 
• 1338332-61-8 uridine 5'-diphospho-2-acetamido-6-phenylacetamido-2,6-dideoxy-α-D-glucopyranoside 
• 1338332-62-9 uridine 5'-diphospho-2-acetamido-6-(1,1'-biphenyl-4-yl)-acetamido-2,6-dideoxy-α-D-glucopyranoside 
• 1109-79-1 uridine 5'-(2-amino-2-deoxy-α-D-glucopyranosyl)-diphosphate 
• 528-04-1 uridine-5'-diphospho-N-acetyl-D-galactosamine 
• 34198-43-1 5-Iodo-UTP 
• 16375-63-6 UDP-6-deoxy-Gal 
• 1435273-16-7 UDP-4-N₃-Gal 

Relevant articles and documents

Nucleoside diphosphokinase of pea seeds.

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Nucleotide promiscuity of 3-phosphoglycerate kinase is in focus: Implications for the design of better anti-HIV analogues

The wide specificity of 3-phosphoglycerate kinase (PGK) towards its nucleotide substrate is a property that allows contribution of this enzyme to the effective phosphorylation (i.e. activation) of nucleotide-based pro-drugs against HIV. Here, the structural basis of the nucleotide-PGK interaction is characterised in comparison to other kinases, namely pyruvate kinase (PK) and creatine kinase (CK), by enzyme kinetic analysis and structural modelling (docking) studies. The results provided evidence for favouring the purine vs. pyrimidine base containing nucleotides for PGK rather than for PK or CK. This is due to the exceptional ability of PGK in forming the hydrophobic contacts of the nucleotide rings that assures the appropriate positioning of the connected phosphate-chain for catalysis. As for the d-/l-configurations of the nucleotides, the l-forms (both purine and pyrimidine) are well accepted by PGK rather than either by PK or CK. Here again the dominance of the hydrophobic interactions of the l-form of pyrimidines with PGK is underlined in comparison with those of PK or CK. Furthermore, for the l-forms, the absence of the ribose OH-groups with PGK is better tolerated for the purine than for the pyrimidine containing compounds. On the other hand, the positioning of the phosphate-chain is an even more important term for PGK in the case of both purines and pyrimidines with an l-configuration, as deduced from the present kinetic studies with various nucleotide-site mutants of PGK. These characteristics of the kinase-nucleotide interactions can provide a guideline for designing new drugs.

An improved one-pot synthesis of nucleoside 5'-triphosphate analogues

Nucleoside 5'-triphosphate (NTP) analogues are valuable tools for biochemical and medicinal research. Therefore, a facile and efficient synthesis of NTP analogues is required. Here, we report on an improved nucleoside 5'-triphosphorylation procedure to obtain pure products after liquid chromotagrpahy (LC) separation with no need for high performance liquid chromatography (HPLC) purification. To improve the selectivity of the reaction we attempted the optimization of several parameters such as solvent, pyrophosphate nucleophilicity, time and temperature of the reaction. Eventually, the reaction was optimized by decreasing the temperature to -15°C and increasing the reaction time to 2 hours, based on monitoring time-dependent product distribution using 31P NMR. Furthermore, the NTPs were obtained as pure products after LC separation, which was impossible in the original Ludwig procedure. Good yields were obtained for all studied natural and synthetic nucleosides.