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68-94-0 Usage

Description

Hypoxanthine is a naturally occurring purine derivative and intermediate in the synthesis of uric acid. It is elevated in the spinal fluid of patients with Lesch-Nyhan syndrome, a metabolic disorder whose symptoms include cerebral palsy, cognitive deficits, motor dysfunction, self-mutilation, and hyperuricemia. Injection of hypoxanthine (10 μM) increases succinate dehydrogenase and complex II activities and decreases cytochrome c oxidase activity, resulting in neuroenergetic impairment, ATP depletion, and cellular apoptosis in rat striatum. It is also used to induce hyperuricemia in mice for use in the development of hypouricemic agents.

Chemical Properties

White to off-white powder

Uses

Different sources of media describe the Uses of 68-94-0 differently. You can refer to the following data:
1. A naturally occurring purine derivative. Pharmaceuticals, Intermediates & Fine Chemicals
2. Hypoxanthine is a nutrient additive for a variety of cell culture applications involving bacterial, parasite (Plasmodium falciparum) and animal cells. Hypoxanthine is a component of selection media used in hybridoma technologies.
3. Hypoxanthine, is used as a marker for energy perturbation in hypoxia/ ischemia. The compound has been used in studies as in indicator, along with uric acid and allantoin , of in vivo free radical reactions. It has been also used in DNA studies to investigate the destabilizing effect it has on DNA duplexes containing hypoxanthine as a base, in a gas phase versus a liquid phase. Hypoxanthine has also been used in studies along with 8-oxoguanine nucleotides to investigate their interaction with human DNA pol ? (DNA polymerase alpha) and DNA polymerase I from Bacillus stearothermophilus. It is also used as a pharmaceutical intermediate.

Definition

ChEBI: A purine nucleobase that consists of purine bearing an oxo substituent at position 6.

General Description

Hypoxanthine (6-hydroxypurine), a purine derivative is a naturally occurring compound. It is the deaminated form of adenine and a breakdown product of adenosine monophosphate (AMP).

Biochem/physiol Actions

Hypoxanthine?is capable of stimulating cell death. It can also induce reactive oxygen species (ROS). It results in endothelial dysfunction via apoptosis, stimulated by oxidative stress.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. When heated to decomposition it emits toxic fumes of Nox

Purification Methods

Crystallise it from hot water and dry it at 105o. [Beilstein 26 II 252, 26 III/IV 2081.]

Check Digit Verification of cas no

The CAS Registry Mumber 68-94-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 8 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 68-94:
(4*6)+(3*8)+(2*9)+(1*4)=70
70 % 10 = 0
So 68-94-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-3H,(H,6,7,8,9,10)

68-94-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (H0311)  Hypoxanthine  >98.0%(HPLC)(E)

  • 68-94-0

  • 5g

  • 245.00CNY

  • Detail
  • TCI America

  • (H0311)  Hypoxanthine  >98.0%(HPLC)(E)

  • 68-94-0

  • 25g

  • 530.00CNY

  • Detail
  • Alfa Aesar

  • (A11481)  Hypoxanthine, 99%   

  • 68-94-0

  • 5g

  • 179.0CNY

  • Detail
  • Alfa Aesar

  • (A11481)  Hypoxanthine, 99%   

  • 68-94-0

  • 25g

  • 601.0CNY

  • Detail
  • Alfa Aesar

  • (A11481)  Hypoxanthine, 99%   

  • 68-94-0

  • 100g

  • 1950.0CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000441)  Didanosine impurity A,  European Pharmacopoeia (EP) Reference Standard

  • 68-94-0

  • Y0000441

  • 1,880.19CNY

  • Detail
  • USP

  • (1191226)  Didanosine Related Compound A  United States Pharmacopeia (USP) Reference Standard

  • 68-94-0

  • 1191226-25MG

  • 13,501.80CNY

  • Detail

68-94-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name hypoxanthine

1.2 Other means of identification

Product number -
Other names 6-Oxopurine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:68-94-0 SDS

68-94-0Synthetic route

formic acid
64-18-6

formic acid

6-chloro-4,5-diaminopyrimidine
4316-98-7

6-chloro-4,5-diaminopyrimidine

A

6-amino-5-formylamino-3H-pyrimidin-4-one
64194-58-7

6-amino-5-formylamino-3H-pyrimidin-4-one

B

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

uric Acid
69-93-2

uric Acid

A

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

B

xanthin
69-89-6

xanthin

Conditions
ConditionsYield
With water at 180 - 200℃;
formic acid
64-18-6

formic acid

5-amino-3-β-D-ribofuranosyl-3H-imidazole-4-carboxylic acid amide
7132-71-0

5-amino-3-β-D-ribofuranosyl-3H-imidazole-4-carboxylic acid amide

acetic anhydride
108-24-7

acetic anhydride

A

7-β-D-ribofuranosyl-1,7-dihydro-purin-6-one
5627-15-6, 5627-18-9, 10280-01-0, 10280-02-1, 19895-30-8

7-β-D-ribofuranosyl-1,7-dihydro-purin-6-one

B

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
und Erwaermen des Reaktionsprodukts mit wss.KHCO3;
5,6-diamino-3H-pyrimidin-4-one; sulfate
52502-66-6, 102783-18-6, 120568-21-0

5,6-diamino-3H-pyrimidin-4-one; sulfate

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With formic acid
acetic anhydride
108-24-7

acetic anhydride

aminomalonamamidine dihydrochloride
16014-63-4

aminomalonamamidine dihydrochloride

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

5,6-diamino-3H-pyrimidin-4-one; sulfate
52502-66-6, 102783-18-6, 120568-21-0

5,6-diamino-3H-pyrimidin-4-one; sulfate

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

N-(5-amino-6-chloropyrimidin-4-yl)formamide
7501-32-8

N-(5-amino-6-chloropyrimidin-4-yl)formamide

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
zeitlicher Verlauf der Hydrolyse.Hydrolysis;
7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
durch Enzymwirkung; z. B. durch faulenden Pankreasextrakt unter Luftabschluss;
durch Faeulnisbakterien;
durch Schweinemilzferment;
ammonium acetate
631-61-8

ammonium acetate

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

ethyl 2-acetamido-2-cyanoacetate
90877-70-6, 4977-62-2

ethyl 2-acetamido-2-cyanoacetate

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With ammonia at 180℃;
chloroform
67-66-3

chloroform

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

xanthin
69-89-6

xanthin

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
at 60 - 70℃;
xanthin
69-89-6

xanthin

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
at 200℃;
xanthin
69-89-6

xanthin

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With sodium hydroxide; chloroform at 60 - 70℃;
With garcinielliptone HA; xanthine oxidase In water at 25℃; for 0.0833333h; pH=7.5; Kinetics; Reagent/catalyst; Time; Concentration; aq. phosphate buffer; Enzymatic reaction;
adenosine
58-61-7

adenosine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
mit Hilfe von Bacterium-coli;
Hydrolyse und Desaminierung bei der Einwirkung von Escherichia coli und anderen Bakterien.Hydrolysis;
Conditions
ConditionsYield
With nucleoside phosphorylase
With Pi; nucleoside phosphorylase (enzyme) Rate constant;
1,7-dihydro-<1 or 3-15N>purin-6-one

1,7-dihydro-<1 or 3-15N>purin-6-one

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

1,7-dihydro-<4-14C>purin-6-one

1,7-dihydro-<4-14C>purin-6-one

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

1,7-dihydro-<8-14C>purin6-one

1,7-dihydro-<8-14C>purin6-one

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

2.8-dichloro-6-ethoxy-purine

2.8-dichloro-6-ethoxy-purine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With phosphorous; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphonium iodide; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphorous; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphonium iodide; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
2.8-dichloro-6-oxy-purine

2.8-dichloro-6-oxy-purine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With phosphonium iodide; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphorous; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphorous; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
With phosphonium iodide; hydrogen iodide at 25℃; durch nachfolgendes Erwaermen auf dem Wasserbad;
2-mercapto-adenine

2-mercapto-adenine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With nitric acid
2-thio-xanthine

2-thio-xanthine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With nitric acid
6-amino-3,7-dihydro-purine-2-thione
3647-48-1

6-amino-3,7-dihydro-purine-2-thione

nitric acid
7697-37-2

nitric acid

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

2-thioxanthine
2487-40-3

2-thioxanthine

nitric acid
7697-37-2

nitric acid

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

2-formylamino-malonomonoimidic acid diamide hydrochloride

2-formylamino-malonomonoimidic acid diamide hydrochloride

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
at 185℃;
sodium ethanolate
141-52-6

sodium ethanolate

5-amino-1(3)H-imidazole-4-carboxylic acid formylamide

5-amino-1(3)H-imidazole-4-carboxylic acid formylamide

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With ethanol
With potassium hydrogencarbonate
5-amino-1(3)H-imidazole-4-carboxylic acid

5-amino-1(3)H-imidazole-4-carboxylic acid

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
at 185℃;
AMP

AMP

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

Conditions
ConditionsYield
mit Hilfe von Bacterium-coli;
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

6-chloropurine hydrochloride

6-chloropurine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; trichlorophosphate In dichloromethane; N,N-dimethyl-aniline99%
furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

kinetin
525-79-1

kinetin

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 72h;90%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 72h;90 % Chromat.
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

13C5-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose
503173-75-9

13C5-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose

[ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)hypoxanthine
503173-78-2

[ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)hypoxanthine

Conditions
ConditionsYield
Stage #1: 1,7-dihydro-6H-purin-6-one With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane Heating;
Stage #2: 13C5-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In dichloromethane for 2.5h; Heating;
86%
copper(II) perchlorate hexahydrate

copper(II) perchlorate hexahydrate

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

[(Cu(tris(2-aminoethyl)amine))2(hypoxanthinato)](ClO4)3

[(Cu(tris(2-aminoethyl)amine))2(hypoxanthinato)](ClO4)3

Conditions
ConditionsYield
With NaOH In methanol; water an aq. soln. of hypoxanthine and a MeOH soln. of N(C2H4NH2)3 and Cu saltmixed, pH adjusted to 8-9 with NaOH soln.; crystd. at room temp. for 3 wk; elem. anal.;81%
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

6-chloropurine methanesulfonate
88166-56-7

6-chloropurine methanesulfonate

Conditions
ConditionsYield
With trichlorophosphate In methanesulfonic acid; dichloromethane; N,N-dimethyl-aniline78%
zinc perchlorate

zinc perchlorate

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

[Zn(tris(2-aminoethyl)amine)(hypoxanthinato)]ClO4*H2O
1145782-16-6

[Zn(tris(2-aminoethyl)amine)(hypoxanthinato)]ClO4*H2O

Conditions
ConditionsYield
With NaOH In methanol; water an aq. soln. of hypoxanthine and a MeOH soln. of N(C2H4NH2)3 and Zn saltmixed, pH adjusted to 8-9 with NaOH soln.; crystd. at room temp. for 3 wk; elem. anal.;78%
cadmium(II) perchlorate hexahydrate

cadmium(II) perchlorate hexahydrate

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

[(Cd(tris(2-aminoethyl)amine))2(hypoxanthinato)](ClO4)3*0.5H2O

[(Cd(tris(2-aminoethyl)amine))2(hypoxanthinato)](ClO4)3*0.5H2O

Conditions
ConditionsYield
With NaOH In methanol; water an aq. soln. of hypoxanthine and a MeOH soln. of N(C2H4NH2)3 and Cd saltmixed, pH adjusted to 8-9 with NaOH soln.; crystd. at room temp. for 1 mo; elem. anal.;54%
bromobenzene
108-86-1

bromobenzene

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

A

1,9-dihydro-9-phenyl-6H-purin-6-one
6334-42-5

1,9-dihydro-9-phenyl-6H-purin-6-one

B

7-phenylhypoxanthine
62382-64-3

7-phenylhypoxanthine

Conditions
ConditionsYield
With N4,N7-bis(2-hydroxyethyl)-1,10-phenanthroline-4,7-diamine; potassium hydroxide; copper(I) bromide In water; N,N-dimethyl-formamide at 120℃; for 32h; Inert atmosphere; Sealed tube; regioselective reaction;A 48%
B 11%
iodobenzene
591-50-4

iodobenzene

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

A

1,9-dihydro-9-phenyl-6H-purin-6-one
6334-42-5

1,9-dihydro-9-phenyl-6H-purin-6-one

B

7-phenylhypoxanthine
62382-64-3

7-phenylhypoxanthine

Conditions
ConditionsYield
With N4,N7-bis(2-hydroxyethyl)-1,10-phenanthroline-4,7-diamine; potassium hydroxide; copper(I) bromide In water; N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere; Sealed tube; regioselective reaction;A 43%
B 14%
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

isopropyl alcohol
67-63-0

isopropyl alcohol

4C5H2N4O(2-)*4C3H8O*5Li(1+)*3H(1+)

4C5H2N4O(2-)*4C3H8O*5Li(1+)*3H(1+)

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; lithium tert-butoxide In N,N-dimethyl-formamide at 100℃; for 72h;31%
ethanol
64-17-5

ethanol

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

4C5H2N4O(2-)*4C2H6O*5Li(1+)*3H(1+)

4C5H2N4O(2-)*4C2H6O*5Li(1+)*3H(1+)

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; lithium tert-butoxide In N,N-dimethyl-formamide at 100℃; for 72h;13%
O-methylcaprolactim
2525-16-8

O-methylcaprolactim

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

1,7-dimethylhypoxanthine
33155-83-8

1,7-dimethylhypoxanthine

7-ethoxy-3,4,5,6-tetrahydro-2H-azepine
13414-33-0

7-ethoxy-3,4,5,6-tetrahydro-2H-azepine

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

1,7-diethyl-1,7-dihydro-purin-6-one
113977-05-2

1,7-diethyl-1,7-dihydro-purin-6-one

4-diazobenzenesulfonic acid
305-80-6

4-diazobenzenesulfonic acid

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

4-(6-oxo-6,7-dihydro-1H-purin-8-ylazo)-benzenesulfonic acid

4-(6-oxo-6,7-dihydro-1H-purin-8-ylazo)-benzenesulfonic acid

1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

5-phosphoribosyl-1-pyrophosphate
97-55-2, 7540-64-9, 99945-37-6, 130384-52-0

5-phosphoribosyl-1-pyrophosphate

[5']inosinic acid
21214-07-3

[5']inosinic acid

Conditions
ConditionsYield
mit Hypoxanthin-phosphoribosyltransferase aus Hefe bzw.Rinderleber;
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

triethylamine
121-44-8

triethylamine

6-diethylaminopurine
6284-24-8

6-diethylaminopurine

Conditions
ConditionsYield
With trichlorophosphate
Conditions
ConditionsYield
mit Enzym-Praeparat aus Rinderleber bzw. aus Taubenleber;
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

methyl iodide
74-88-4

methyl iodide

1,7-dimethyl-1,7-dihydro-purin-6-one; sodium iodide compound

1,7-dimethyl-1,7-dihydro-purin-6-one; sodium iodide compound

Conditions
ConditionsYield
With sodium hydroxide
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

6H-purine-6-thione
50-44-2

6H-purine-6-thione

Conditions
ConditionsYield
With tetraphosphorus decasulfide; tetralin
With pyridine; tetraphosphorus decasulfide
Multi-step reaction with 2 steps
1: N,N-dimethyl-aniline; POCl3
2: ethanol
View Scheme
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

uric Acid
69-93-2

uric Acid

Conditions
ConditionsYield
With oxygen In various solvent(s) Kinetics; Km, Ki,slope, Vmax; xanthine oxidase;
With bovine spleen-extract; oxygen
With oxygen
1,7-dihydro-6H-purin-6-one
68-94-0

1,7-dihydro-6H-purin-6-one

[5']inosinic acid
21214-07-3

[5']inosinic acid

Conditions
ConditionsYield
With by means of cultures of a(n) bacillus subtilis-mutant

68-94-0Relevant articles and documents

The inhibitory effect of citrus flavonoids naringenin and hesperetin against purine nucleoside phosphorylase: Spectroscopic, atomic force microscopy and molecular modeling studies

Gong, Deming,Lv, Xingang,Ren, Er-Fang,Wang, Lang-Hong,Wang, Qilei

, (2020)

In this work, the inhibitory effect of two citrus flavonoids naringenin and hesperetin on human purine nucleoside phosphorylase (hPNP) and their binding mechanism were evaluated. Results from enzymatic kinetics revealed that naringenin and hesperetin reversibly inhibited hPNP via a mixed-type manner with IC50 values of 4.83 × 10?4 M and 5.32 × 10?4 M, respectively. Analysis of molecular modeling revealed that both naringenin and hesperetin bound directly into the active site by generating multiple forces including hydrogen bonding, π–π and π-Alkyl interactions with His64, Glu201, Ser220, His257, Phe200 and Val217 residues of hPNP, which caused the inhibition of hPNP activity. Moreover, conformational analysis by three-dimension fluorescence, circular dichroism and atomic force microscopy revealed that the binding of naringenin and hesperetin to hPNP induced changes in the microenvironment, secondary structure and morphology of hPNP. These results suggested that occupying the active site and enzymatic conformational perturbation induced by naringenin and hesperetin are the main reasons for reducing the inhibition of hPNP activity, which would be helpful in understanding the inhibitory mechanism of naringenin and hesperetin against hPNP.

Calcium-stimulated guanosine-inosine nucleosidase from yellow lupin (Lupinus luteus)

Szuwart, Maciej,Starzynska, Elzbieta,Pietrowska-Borek, Malgorzata,Guranowski, Andrzej

, p. 1476 - 1485 (2006)

Guanosine-inosine-preferring nucleoside N-ribohydrolase has been purified to homogeneity from yellow lupin (Lupinus luteus) seeds by ammonium sulfate fractionation, ion-exchange chromatography and gel filtration. The enzyme functions as a monomeric, 80 kDa polypeptide, most effectively between pH 4.7 and 5.5. Of various mono- and divalent cations tested, Ca2+ appeared to stimulate enzyme activity. The nucleosidase was activated 6-fold by 2 mM exogenous CaCl2 or Ca(NO3)2, with Ka = 0.5 mM (estimated for CaCl2). The Km values estimated for guanosine and inosine were 2.7 ± 0.3 μM. Guanosine was hydrolyzed 12% faster than inosine while adenosine and xanthosine were poor substrates. 2′-Deoxyguanosine, 2′-deoxyinosine, 2′-methylguanosine, pyrimidine nucleosides and 5′-GMP were not hydrolyzed. However, the enzyme efficiently liberated the corresponding bases from synthetic nucleosides, such as 1-methylguanosine, 7-methylguanosine, 1-N2-ethenoguanosine and 1-N2-isopropenoguanosine, but hydrolyzed poorly the ribosides of 6-methylaminopurine and 2,6-diaminopurine. MnCl2 or ZnCl2 inhibited the hydrolysis of guanosine with I50 ≈ 60 μM. Whereas 2′-deoxyguanosine, 2′-methylguanosine, adenosine, as well as guanine were competitive inhibitors of this reaction (Ki values were 1.5, 3.6, 21 and 9.7 μM, respectively), hypoxanthine was a weaker inhibitor (Ki = 64 μM). Adenine, ribose, 2-deoxyribose, 5′-GMP and pyrimidine nucleosides did not inhibit the enzyme. The guanosine-inosine hydrolase activity occurred in all parts of lupin seedlings and in cotyledons it increased up to 5-fold during seed germination, reaching maximum in the third/fourth day. The lupin nucleosidase has been compared with other nucleosidases.

-

Taylor,Cheng

, p. 9. (1959)

-

Assay of purine nucleoside phosphorylase in erythrocytes by flow-injection analysis with fluorescence detection

Hayashi,Zaitsu,Ohkura

, p. 4574 - 4578 (1987)

-

Phloroglucinols Inhibit Chemical Mediators and Xanthine Oxidase, and Protect Cisplatin-Induced Cell Death by Reducing Reactive Oxygen Species in Normal Human Urothelial and Bladder Cancer Cells

Lin, Kai-Wei,Huang, A.-Mei,Tu, Huang-Yao,Weng, Jing-R.U.,Hour, Tzyh-Chyuan,Wei, Bai-Luh,Yang, Shyh-Chyun,Wang, Jih-Pyang,Pu, Yeong-Shiau,Lin, Chun-Nan

, p. 8782 - 8787 (2009)

Phloroglucinols, garcinielliptones HA-HE (1-5), and C (6) were studied in vitro for their inhibitory effects on chemical mediators released from mast cells, neutrophils, and macrophages. Compound 6 revealed significant inhibitory effect on release of lysozyme from rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB). Compounds 3, 4, and 6 showed significant inhibitory effects on superoxide anion generation in rat neutrophils stimulated with (fMLP)/(CB), while compounds 1 and 5 revealed inhibitory effects on tumor necrosis factor-α (TNF-α) formation in macrophages stimulated with lipopolysaccharide (LPS). Compounds 1 and 3-6 showed inhibitory effects on xanthine oxidase (XO) and could inhibit the DNA breakage caused by O2-.. Treatment of NTUB1 with 2 to 60 μM compound 3 and 5 μM cisplatin and SV-HUC1 with 9 to 60 μM 3 and 5 μM cisplatin, respectively, resulted in an increase of viability of cells. These results indicated that compounds 1 and 3-6 showed anti-inflammatory effects and antioxidant activities. Compound 3 mediates through the suppression of XO activity and reduction of reactive oxygen species (ROS), and protection of subsequent cell death.

Thermodynamic Reaction Control of Nucleoside Phosphorolysis

Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias

supporting information, p. 867 - 876 (2020/01/24)

Nucleoside analogs represent a class of important drugs for cancer and antiviral treatments. Nucleoside phosphorylases (NPases) catalyze the phosphorolysis of nucleosides and are widely employed for the synthesis of pentose-1-phosphates and nucleoside analogs, which are difficult to access via conventional synthetic methods. However, for the vast majority of nucleosides, it has been observed that either no or incomplete conversion of the starting materials is achieved in NPase-catalyzed reactions. For some substrates, it has been shown that these reactions are reversible equilibrium reactions that adhere to the law of mass action. In this contribution, we broadly demonstrate that nucleoside phosphorolysis is a thermodynamically controlled endothermic reaction that proceeds to a reaction equilibrium dictated by the substrate-specific equilibrium constant of phosphorolysis, irrespective of the type or amount of NPase used, as shown by several examples. Furthermore, we explored the temperature-dependency of nucleoside phosphorolysis equilibrium states and provide the apparent transformed reaction enthalpy and apparent transformed reaction entropy for 24 nucleosides, confirming that these conversions are thermodynamically controlled endothermic reactions. This data allows calculation of the Gibbs free energy and, consequently, the equilibrium constant of phosphorolysis at any given reaction temperature. Overall, our investigations revealed that pyrimidine nucleosides are generally more susceptible to phosphorolysis than purine nucleosides. The data disclosed in this work allow the accurate prediction of phosphorolysis or transglycosylation yields for a range of pyrimidine and purine nucleosides and thus serve to empower further research in the field of nucleoside biocatalysis. (Figure presented.).

The Chemoenzymatic Synthesis of 2-Chloro- and 2-Fluorocordycepins

Denisova, Alexandra O.,Tokunova, Yulia A.,Fateev, Ilja V.,Breslav, Alexandra A.,Leonov, Vladimir N.,Dorofeeva, Elena V.,Lutonina, Olga I.,Muzyka, Inessa S.,Esipov, Roman S.,Kayushin, Alexey L.,Konstantinova, Irina D.,Miroshnikov, Anatoly I.,Stepchenko, Vladimir A.,Mikhailopulo, Igor A.

, p. 4853 - 4860 (2017/10/06)

Two approaches to the chemoenzymatic synthesis of 2-fluorocordycepin and 2-chlorocordycepin were studied: (i) the use of 3′-deoxyadenosine (cordycepin) and 3′-deoxyinosine (3′dIno) as donors of 3-deoxy- d -ribofuranose in the transglycosylation of 2-fluoro- (2F Ade) and 2-chloroadenine (2Cl Ade) catalyzed by the recombinant E. coli purine nucleoside phosphorylase (PNP), and (ii) the use of 2-fluoroadenosine and 3′-deoxyinosine as substrates of the cross-glycosylation and PNP as a biocatalyst. An efficient method for 3′-deoxyinosine synthesis starting from inosine was developed. However, the very poor solubility of 2Cl Ade and 2F Ade is the limiting factor of the first approach. The second approach enables this problem to be overcome and it appears to be advantageous over the former approach from the viewpoint of practical synthesis of the title nucleosides. The 3-deoxy-α- d -ribofuranose-1-phosphate intermediary formed in the 3′dIno phosphorolysis by PNP was found to be the weak and marginal substrate of E. coli thymidine (TP) and uridine (UP) phosphorylases, respectively. Finally, one-pot cascade transformation of 3-deoxy- d -ribose in cordycepin in the presence of adenine and E. coli ribokinase, phosphopentomutase, and PNP was tested and cordycepin formation in ca. 3.4% yield was proved.

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