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61-19-8 Usage

Chemical Properties

White crystalline powder. Melting point: 196-200°C (decomposition). Specific optical rotation:-47.5° (20°C, 2% in sodium hydroxide (2%)). Soluble in water, slightly soluble in alcohol, insoluble in ether.

Applications

Clinically it is used to treat disseminated sclerosis, porphyria, itching, liver disease, varicose ulcer complication. Eye drops with denosine monophosphate as the main component can be used to treat eye fatigue, central amphiblestitis, ocular pannus,? herpes and other corneal surface diseases. Intramuscular injection shows local erythema, generalized essential telangiectasia, red face, dizziness, breathing difficulty and palpitation. As nutrition enhancer; as intermediate to produce nucleotide drugs; as food additive; as biological products; as dietary supplement and biochemical reagent. It is used to produce adenosine triphosphate (ATP), cyclic adenylate (cAMP) and other biochemical drugs. It is a type of nucleotide products and to produce antiviral drugs, synthetic energy drugs and cardiovascular and cerebrovascular drugs, such as adenosine, ATP, 3 '-5'-cyclic adenosine monophosphate.

Preparation

Candida utilis fungi is treated with hot water to obtain nucleic acids, which is hydrolyzed by enzymes and separated to obtain the final product. Take mycelia as the raw material: Subtraction and sedimentation of mycelia are carried out with 3 times amount of water. Industry base is added to reach a base concentration of 0.25% (g/100mL). After stirring for 1 hours, 20% sulfuric acid is added until the PH value is 7. The solution is filtrated and the pH value of filtrate is adjusted with 20% sulfuric acid to 2.5. Centrifugation is then applied to obtain nucleic acid mud. mycelia [sodium hydroxide]→[1h] extract solution [20% sulfuric acid] → [pH=7, filtration] filtrate [20% sulfuric acid] →[pH=2.5, centrifugation] nucleic acid mud 1% nucleic acid solution is made by subsequent dissolution, enzymolysis, absorption and elution. 10% ammonia water is then used to adjust the pH value to 6-6.2. Then the mixture is heated at 90°C for 20 min and cooled. After centrifugation, the supernatant is heated up to 65-70°C and added with 1/3 phosphodiesterase solution. After 2 hours, the temperature is raised to 90°C.? 10min later, it is cooled to room temperature. 20% sulfuric acid is added to adjust the pH value to 2.5-3. After filtration, the filtrate is adjusted with ammonia solution until the pH=7.2-7.5. 0.3% (3 g/L) diatomite is then added to assist the filtration. The corresponding supernatant is filtered with an anion exchange resin column (717-type) and eluted with 0.05 mol/L sulfuric acid. Afterwards, absorption, elution and crystallization are carried out. The detailed procedures of these three steps are: The eluate is first absorbed with a cation exchange column (732-type) and eluted with distilled water (pH=1.5). The collection of eluate starts when the eluate turned red with bromine water. The eluate is then concentrated to 80-90 mg/mL under reduced pressure, added with diatomite and stirred for 30 min before filtration. The filtrate is adjusted with 6 mol/L hydrochloric acid till pH=2.5. To realize full crystallization, the filtrate is cooled during stirring. After followed filtration, it is washed with dry ethanol for 3 times. Vacuum drying at 60°C is applied to obtain the final AMP products. Nucleic acid mud [ammonia gas] →[pH=6-6.2, 90°C, 20min] supernatant [phosphodiesterase] →[65-70°C,2h,] hydrolysis solution [717 resin] →absorbent [sulfuric acid] →elution solution [732 resin] →AMP, CMP, GMP absorbent mixtures.

Usage restriction

GB 2760-2001:infant formula milk powder 0.2~0.58 g/kg (based on the total amount of nucleotide)

Toxicity Grading

Middle toxicity

Acute Toxicity

Peritoneal-mouse LD50: 4000 mg/kg

Flammability Hazardous Characteristics

Flammable; generation of toxic nitrogen oxides and phosphorous oxide smoke when heated.

Storage and Transport

Stored in well ventilated area, low temperature, and dry.

Extinguishing Agent

Dry powder, foam, sand, carbon dioxide.

Description

Adenosine-5'-monophosphoric acid is a nucleotide that is synthesized from adenosine triphosphate and inosine monophosphate. Adenosine-5'-monophosphoric acid is an important molecule in the body because it is a substrate for cyclic AMP, which regulates many cellular processes. Adenosine-5'-monophosphoric acid also has biochemical properties that are similar to those of the neurotransmitter serotonin and it can activate the 5-HT2 receptors.

Uses

Different sources of media describe the Uses of 61-19-8 differently. You can refer to the following data:
1. vasodilator, neuromodulator
2. A useful ligand determinant that facilitates the binding of APS reductase inhibitors.
3. Adenosine 5'-monophosphate is a nucleotide (building blocks of nucleic acid) added to skin care products to bind water and moisture.

Definition

ChEBI: A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.

Brand name

Adenyl (Wyeth-Ayerst); My-BDen (Bayer.

Biological Activity

adenosine 5'-monophosphate is an ester of phosphoric acid with the nucleoside adenosine.

Safety Profile

Slightly toxic by intraperitoneal route. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of PO, and NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 61-19-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 1 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 61-19:
(4*6)+(3*1)+(2*1)+(1*9)=38
38 % 10 = 8
So 61-19-8 is a valid CAS Registry Number.

61-19-8 Well-known Company Product Price

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

  • (A0158)  5'-Adenylic Acid  >98.0%(HPLC)(T)

  • 61-19-8

  • 1g

  • 105.00CNY

  • Detail
  • TCI America

  • (A0158)  5'-Adenylic Acid  >98.0%(HPLC)(T)

  • 61-19-8

  • 5g

  • 360.00CNY

  • Detail
  • TCI America

  • (A0158)  5'-Adenylic Acid  >98.0%(HPLC)(T)

  • 61-19-8

  • 25g

  • 1,280.00CNY

  • Detail
  • Alfa Aesar

  • (L14051)  Adenosine-5'-monophosphoric acid, 99% (dry wt.), water <6%   

  • 61-19-8

  • 1g

  • 179.0CNY

  • Detail
  • Alfa Aesar

  • (L14051)  Adenosine-5'-monophosphoric acid, 99% (dry wt.), water <6%   

  • 61-19-8

  • 5g

  • 608.0CNY

  • Detail
  • USP

  • (1012178)  5′-Adenylicacid  United States Pharmacopeia (USP) Reference Standard

  • 61-19-8

  • 1012178-500MG

  • 4,647.24CNY

  • Detail

61-19-8SDS

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 AMP

1.2 Other means of identification

Product number -
Other names myoston

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:61-19-8 SDS

61-19-8Synthetic route

5,6-dimethyl-1H-benzotriazole adenine dinucleotide ammonium salt

5,6-dimethyl-1H-benzotriazole adenine dinucleotide ammonium salt

A

5,6-dimethyl-1H-benzotriazole mononucleotide ammonium salt
123499-60-5

5,6-dimethyl-1H-benzotriazole mononucleotide ammonium salt

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With phosphodiesterase; tris hydrochloride; magnesium chloride In water at 37℃; for 5h; pH: 9.0;A 99%
B n/a
adenosine-5'-monophosphate disodium salt
4578-31-8

adenosine-5'-monophosphate disodium salt

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With Dowex 50W×8 resin In water at 20℃; for 0.5h;99%
With Dowex 50WX-8 200 mesh, H+
5-methyl-1H-benzotriazole adenine dinucleotide ammonium salt

5-methyl-1H-benzotriazole adenine dinucleotide ammonium salt

A

5-methyl-1H-benzotriazole mononucleotide ammonium salt
123499-59-2

5-methyl-1H-benzotriazole mononucleotide ammonium salt

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With phosphodiesterase; tris hydrochloride; magnesium chloride In water at 37℃; for 10h; pH: 9.0;A 98%
B n/a
5-nitro-1H-benzotriazole adenine dinucleotide ammonium salt

5-nitro-1H-benzotriazole adenine dinucleotide ammonium salt

A

5-nitro-1H-benzotriazole mononucleotide ammonium salt
123499-62-7

5-nitro-1H-benzotriazole mononucleotide ammonium salt

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With phosphodiesterase; tris hydrochloride; magnesium chloride In water at 37℃; for 10h; pH: 9.0;A 97%
B n/a
1H-benzotriazole adenine dinucleotide ammonium salt

1H-benzotriazole adenine dinucleotide ammonium salt

A

1H-benzotriazole mononucleotide ammonium salt
123499-58-1

1H-benzotriazole mononucleotide ammonium salt

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With phosphodiesterase; tris hydrochloride; magnesium chloride In water at 37℃; for 12h; pH: 9.0;A 96%
B 0.31 g
adenosine 5'-phosphorimidazolide
20816-58-4, 116273-87-1

adenosine 5'-phosphorimidazolide

A

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

B

adenosine 5'-phosphorofluoride
19375-33-8

adenosine 5'-phosphorofluoride

Conditions
ConditionsYield
With potassium fluoride; water at 25℃; pH=8.6; Kinetics; Reagent/catalyst; pH-value;A 6.5%
B 93.5%
5-chloro-1H-benzotriazole adenine dinucleotide ammonium salt

5-chloro-1H-benzotriazole adenine dinucleotide ammonium salt

A

5-chloro-1H-benzotriazole mononucleotide ammonium salt
123499-61-6

5-chloro-1H-benzotriazole mononucleotide ammonium salt

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With phosphodiesterase; tris hydrochloride; magnesium chloride In water at 37℃; for 5h; pH: 9.0;A 93%
B n/a
8-aza-9H-adenine adenine dinucleotide ammonium salt

8-aza-9H-adenine adenine dinucleotide ammonium salt

A

8-azaadenosine monophosphate ammonium salt
123499-63-8

8-azaadenosine monophosphate ammonium salt

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With phosphodiesterase; tris hydrochloride; magnesium chloride In water at 37℃; for 6h; pH: 9.0;A 87%
B n/a
adenosine
58-61-7

adenosine

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
Stage #1: adenosine With trichlorophosphate at 20℃; for 0.1h; Flow reactor; Green chemistry;
Stage #2: With water at 20℃; Temperature; Flow reactor; Green chemistry; chemoselective reaction;
86%
With tris(p-nitrophenyl)phosphate at 50℃; Erwina herbicola 47/3 cells;65%
With trichlorophosphate In water for 0.5h; Solvent;27%
Morpholin-4-yl-phosphonic acid mono-{(3aR,4R,6R,6aR)-2-methoxy-6-[6-(4-methoxy-phenylamino)-purin-9-yl]-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl} ester

Morpholin-4-yl-phosphonic acid mono-{(3aR,4R,6R,6aR)-2-methoxy-6-[6-(4-methoxy-phenylamino)-purin-9-yl]-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl} ester

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With 1,4-dioxane; ammonium hydroxide at 20℃; for 60h;85%
D-luciferyl adenylate

D-luciferyl adenylate

A

4-hydroxyluciferin

4-hydroxyluciferin

B

4-hydroxyluciferyl adenylate

4-hydroxyluciferyl adenylate

C

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With 5'-CTGCGATTTTAAGTGTGGTACCATTCCATTGCGGTTTTGGAATGTTTAC-3'; ATP magnesium salt In aq. phosphate buffer at 22℃; for 0.00833333h; pH=7.8; Reagent/catalyst;A n/a
B 81%
C 27%
Phosphoric acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester bis-(2,2,2-tribromo-ethyl) ester
78681-86-4

Phosphoric acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester bis-(2,2,2-tribromo-ethyl) ester

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With Nafion 125; lithium perchlorate In N,N-dimethyl-formamide; acetonitrile electrolysis;80%
D-luciferyl adenylate

D-luciferyl adenylate

A

4-hydroxyluciferin

4-hydroxyluciferin

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With pyralis luciferase; ATP magnesium salt In aq. phosphate buffer at 22℃; pH=7.8; Reagent/catalyst;A 79%
B 30%
23,24-Bisnorchola-1,4-dien-3-one-22-carboxylic acid
3614-61-7, 5327-60-6, 66512-12-7, 96686-97-4, 14508-05-5

23,24-Bisnorchola-1,4-dien-3-one-22-carboxylic acid

coenzyme A
85-61-0

coenzyme A

A

3-oxo-23,24-bisnorchol-4-en-22-oyl-coenzyme A
1380518-01-3

3-oxo-23,24-bisnorchol-4-en-22-oyl-coenzyme A

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With recombinant Rhodococcus jostii RHA1 CasI; magnesium chloride In ethanol at 22℃; for 7h; pH=7.5; aq. buffer; Enzymatic reaction;A 75%
B n/a
triethylamine carbonate
15715-58-9

triethylamine carbonate

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate
24558-92-7

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate

thymidine 5'-phosphate sodium salt
33430-62-5, 61240-13-9, 75652-49-2, 85597-60-0

thymidine 5'-phosphate sodium salt

A

P1-(adenosin-5'-yl)-P2-(thymidin-5'''-yl) bis(triethylammonium) salt

P1-(adenosin-5'-yl)-P2-(thymidin-5'''-yl) bis(triethylammonium) salt

B

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

C

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
Stage #1: N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate; thymidine 5'-phosphate sodium salt With 1H-tetrazole; magnesium(II) chloride hexahydrate; water at 20℃; for 1.5h; in ball mill;
Stage #2: triethylamine carbonate In water; acetonitrile pH=8.2;
A 71%
B n/a
C n/a

A

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

B

adenosine 5'-diphosphate
58-64-0

adenosine 5'-diphosphate

Conditions
ConditionsYield
hexaazadioxomacrocycle (<24>-N6O2); calcium bromide In water; water-d2 at 70℃; for 0.583333h; Rate constant; Product distribution; pH 7.6; var. MBr2 salts; standing 24 h at rt.;A 10%
B 70%
With water; caesium carbonate In dimethyl sulfoxide at 125℃; for 0.0833333h; Product distribution; Further Variations:; Solvents; Reagents; Temperatures; microwave irradiation;
nicotinamide mononucleotide
1094-61-7

nicotinamide mononucleotide

triethylamine carbonate
15715-58-9

triethylamine carbonate

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate
24558-92-7

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate

A

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

B

0.2CH2O3*1.2C6H15N*C21H27N7O14P2

0.2CH2O3*1.2C6H15N*C21H27N7O14P2

C

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
Stage #1: nicotinamide mononucleotide; N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate With 1H-tetrazole; magnesium(II) chloride hexahydrate; water at 20℃; for 1.5h; in ball mill;
Stage #2: triethylamine carbonate In water; acetonitrile pH=8.2;
A n/a
B 58%
C n/a
triethylamine carbonate
15715-58-9

triethylamine carbonate

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate
24558-92-7

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate

adenosine 5'-triphosphate disodium salt

adenosine 5'-triphosphate disodium salt

A

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

B

0.6CH2O3*4.6C6H15N*C20H28N10O19P4

0.6CH2O3*4.6C6H15N*C20H28N10O19P4

C

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
Stage #1: N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate; adenosine 5'-triphosphate disodium salt With 1H-tetrazole; magnesium(II) chloride hexahydrate; water at 20℃; for 1.5h; in ball mill;
Stage #2: triethylamine carbonate In water; acetonitrile pH=8.2;
A n/a
B 52%
C n/a
bromocyane
506-68-3

bromocyane

Adenosine 5'<(S)α-thio>diphosphate
59286-20-3

Adenosine 5'<(S)α-thio>diphosphate

A

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

B

adenosine 5'-diphosphate
58-64-0

adenosine 5'-diphosphate

Conditions
ConditionsYield
With potassium hydroxide; rac-cysteine; 18O-labeled water Mechanism; 18O and 17O labeled experiment, also with (SP)-adenosine- 5'-O-(2-thiotriphosphate), other products;A 50%
B 20%
triethylamine carbonate
15715-58-9

triethylamine carbonate

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate
24558-92-7

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate

ADP*H1.6*Na1.4

ADP*H1.6*Na1.4

A

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

B

1.5CH2O3*4.5C6H15N*C20H27N10O16P3

1.5CH2O3*4.5C6H15N*C20H27N10O16P3

C

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
Stage #1: N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate; ADP*H1.6*Na1.4 With 1H-tetrazole; magnesium(II) chloride hexahydrate; water at 20℃; for 1.5h; in ball mill;
Stage #2: triethylamine carbonate In water; acetonitrile pH=8.2;
A n/a
B 49%
C n/a
triethylamine carbonate
15715-58-9

triethylamine carbonate

ribose-5-monophosphate barium salt
24325-23-3, 108321-98-8

ribose-5-monophosphate barium salt

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate
24558-92-7

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate

A

P1-(adenosin-5'-yl)-P2-(ribos-5''-yl) bis(triethylammonium) salt

P1-(adenosin-5'-yl)-P2-(ribos-5''-yl) bis(triethylammonium) salt

B

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt

C

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
Stage #1: ribose-5-monophosphate barium salt; N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate With 1H-tetrazole; magnesium(II) chloride hexahydrate; water at 20℃; for 1.5h; in ball mill;
Stage #2: triethylamine carbonate In water; acetonitrile pH=8.2;
A 43%
B n/a
C n/a
N-(purine-6-yl)-L-aspartic acid 9-β-D-ribofuranoside-5'-phosphate
19046-78-7

N-(purine-6-yl)-L-aspartic acid 9-β-D-ribofuranoside-5'-phosphate

A

acetaldehyde
75-07-0

acetaldehyde

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With copper(I) sulfate; ammonium acetate; oxygen In various solvent(s) at 100℃; for 5h; Product distribution; further reagent, without O2;A n/a
B 25%
C16H17BrN7O7P
77079-61-9

C16H17BrN7O7P

A

8-(4-bromophenyl)adenine
77071-04-6

8-(4-bromophenyl)adenine

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With sodium hydroxide at 90℃; for 72h; pH 9-10;A 14%
B n/a

A

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

B

adenosine 5'-phosphorofluoride
19375-33-8

adenosine 5'-phosphorofluoride

Conditions
ConditionsYield
With water; sodium fluoride at 25℃; pH=5.5; Kinetics; pH-value;A 8.6%
B 1.8%
cAMP
60-92-4

cAMP

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With cerium(III) chloride; water at 30℃; Rate constant; Mechanism; pH 8.0; velocity const. - var. pH's dependence;
With buffer pH 7; tris(3-aminopropyl)amine cobalt(III) hydroxo aqua at 25℃; relative rates of hydrolysis to the monoesters 3'-AMP and 5'-AMP; var. cobalt(III)-complexes;
With hydrogenchloride at 90.1℃; Rate constant;
L-Aspartic acid
56-84-8

L-Aspartic acid

[5']inosinic acid
21214-07-3

[5']inosinic acid

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
Biosynthese;
[5']inosinic acid
21214-07-3

[5']inosinic acid

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
enzymatische Ueberfuehrung;
2',3'-di-O-acetyladenosine
29886-19-9

2',3'-di-O-acetyladenosine

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
ueber mehrere Stufen;
2',3'-Isopropylidene-5'-AMP
20408-44-0

2',3'-Isopropylidene-5'-AMP

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With hydrogenchloride at 25℃; for 12h; Yield given;
With formic acid at 25℃; for 18h; Yield given;
With DOWEX(R) 50WX2-200
With sulfuric acid
2-chloroethanal
107-20-0

2-chloroethanal

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

N6-Etheno-AMP
37482-16-9

N6-Etheno-AMP

Conditions
ConditionsYield
With sodium acetate In water at 37℃; for 12h;99%
In aq. phosphate buffer at 100℃; for 0.25h; Temperature;
morpholine
110-91-8

morpholine

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

adenosine 5'-phosphoromorpholidate sodium salt
95314-00-4

adenosine 5'-phosphoromorpholidate sodium salt

Conditions
ConditionsYield
With 2,2'-dipyridyldisulphide; triphenylphosphine; sodium iodide In dimethyl sulfoxide for 0.666667h; Ambient temperature;98%
5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

O2'-(toluene-4-sulfonyl)-[5']adenylic acid
28220-12-4

O2'-(toluene-4-sulfonyl)-[5']adenylic acid

Conditions
ConditionsYield
Stage #1: 5'-adenosine monophosphate With sodium hydroxide In 1,4-dioxane at 5 - 15℃; for 0.5h;
Stage #2: p-toluenesulfonyl chloride In 1,4-dioxane at -15 - 5℃; for 18h;
97.6%
2-methylimidazole
693-98-1

2-methylimidazole

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

adenosine 5'-[sodium (2-methyl-1H-imidazol-1-yl)phosphonate]

adenosine 5'-[sodium (2-methyl-1H-imidazol-1-yl)phosphonate]

Conditions
ConditionsYield
With 2,2'-dipyridyldisulphide; triethylamine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 2h; Condensation;92%
benzaldehyde
100-52-7

benzaldehyde

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

sodium ((3aS,4R,6R,6aS)-6-(6-amino-9H-purin-9-yl)-2-phenyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyldihydrogen phosphate

sodium ((3aS,4R,6R,6aS)-6-(6-amino-9H-purin-9-yl)-2-phenyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyldihydrogen phosphate

Conditions
ConditionsYield
In trifluoroacetic acid at 0 - 5℃; for 7h;92%
methyl (2S)-pyrrolidine carboxylate
2577-48-2

methyl (2S)-pyrrolidine carboxylate

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

prolinyladenosine-5'-monophosphate methylester

prolinyladenosine-5'-monophosphate methylester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In aq. buffer at 25℃; for 8h; pH=6.5;92%
2-methylimidazole
693-98-1

2-methylimidazole

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

C14H17N7O6P(1-)

C14H17N7O6P(1-)

Conditions
ConditionsYield
With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 25℃; for 4h; Inert atmosphere;91%
Stage #1: 2-methylimidazole; 5'-adenosine monophosphate With hydrogenchloride; sodium hydroxide In water pH=5.5;
Stage #2: With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere;
morpholine
110-91-8

morpholine

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

adenosine 5'-monophosphate morpholidate
7331-13-7

adenosine 5'-monophosphate morpholidate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In water; tert-butyl alcohol for 3h; Reflux;90%
With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide for 2h;
dibutylphosphinothioyl bromide

dibutylphosphinothioyl bromide

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

adenosine 5'-phosphoric di-n-butylphosphinothioic anhydride
57816-25-8

adenosine 5'-phosphoric di-n-butylphosphinothioic anhydride

Conditions
ConditionsYield
90%
cis-(N,N-dimethyl-ethylenediamine)diaquaplatinum(II)
41575-66-0

cis-(N,N-dimethyl-ethylenediamine)diaquaplatinum(II)

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

2H(1+)*Pt((CH3)2NC2H4NH2)((NH2)(C5N4H2)CH(CHOH)2CH(CH2PO4)O)2(2-)=Pt((CH3)2NC2H4NH2)(NH2(C5N4H2)CH(CHOH)2CH(CH2HPO4)O)2
104051-46-9

2H(1+)*Pt((CH3)2NC2H4NH2)((NH2)(C5N4H2)CH(CHOH)2CH(CH2PO4)O)2(2-)=Pt((CH3)2NC2H4NH2)(NH2(C5N4H2)CH(CHOH)2CH(CH2HPO4)O)2

Conditions
ConditionsYield
In water; water-d2 pH adjustment (4-8.5); addn. of 0.01 M soln. of 5'AMP; monitoring by (1)H-NMR;90%
morpholine
110-91-8

morpholine

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate
24558-92-7

N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate

Conditions
ConditionsYield
In ethyl acetate; tert-butyl alcohol Heating;90%

61-19-8Relevant articles and documents

Dynamic Exchange of Substituents in a Prebiotic Organocatalyst: Initial Steps towards an Evolutionary System

Bechtel, Maximilian,Closs, Anna C.,Trapp, Oliver

supporting information, (2021/12/01)

All evolutionary biological processes lead to a change in heritable traits over successive generations. The responsible genetic information encoded in DNA is altered, selected, and inherited by mutation of the base sequence. While this is well known at the biological level, an evolutionary change at the molecular level of small organic molecules is unknown but represents an important prerequisite for the emergence of life. Here, we present a class of prebiotic imidazolidine-4-thione organocatalysts able to dynamically change their constitution and potentially capable to form an evolutionary system. These catalysts functionalize their building blocks and dynamically adapt to their (self-modified) environment by mutation of their own structure. Depending on the surrounding conditions, they show pronounced and opposing selectivity in their formation. Remarkably, the preferentially formed species can be associated with different catalytic properties, which enable multiple pathways for the transition from abiotic matter to functional biomolecules.

Reduced nicotinamide mononucleotide is a new and potent nad+ precursor in mammalian cells and mice

Zapata-Pérez, Rubén,Tammaro, Alessandra,Schomakers, Bauke V.,Scantlebery, Angelique M. L.,Denis, Simone,Elfrink, Hyung L.,Giroud-Gerbetant, Judith,Cantó, Carles,López-Leonardo, Carmen,McIntyre, Rebecca L.,van Weeghel, Michel,Sánchez-Ferrer, álvaro,Houtkooper, Riekelt H.

, p. 1 - 17 (2021/03/22)

Nicotinamide adenine dinucleotide (NAD+) homeostasis is constantly compromised due to degradation by NAD+-dependent enzymes. NAD+ replenishment by sup-plementation with the NAD+ precursors nicotinamide mononucleotide (NMN) and nicotinamide riboside (NR) can alleviate this imbalance. However, NMN and NR are limited by their mild effect on the cellular NAD+ pool and the need of high doses. Here, we report a synthesis method of a reduced form of NMN (NMNH), and identify this molecule as a new NAD+ precursor for the first time. We show that NMNH increases NAD+ levels to a much higher extent and faster than NMN or NR, and that it is metabolized through a different, NRK and NAMPT-independent, pathway. We also demonstrate that NMNH reduces damage and accelerates repair in renal tubular epithelial cells upon hypoxia/reoxygenation injury. Finally, we find that NMNH administration in mice causes a rapid and sustained NAD+ surge in whole blood, which is accompanied by increased NAD+ levels in liver, kidney, muscle, brain, brown adipose tissue, and heart, but not in white adipose tissue. Together, our data highlight NMNH as a new NAD+ precursor with therapeutic potential for acute kidney injury, confirm the existence of a novel pathway for the recycling of reduced NAD+ precursors and establish NMNH as a member of the new family of reduced NAD+ precursors.

Intrinsic Apyrase-Like Activity of Cerium-Based Metal–Organic Frameworks (MOFs): Dephosphorylation of Adenosine Tri- and Diphosphate

Gu, Jinlou,Li, Chunzhong,Li, Ke,Yang, Jian

supporting information, p. 22952 - 22956 (2020/10/23)

Apyrase is an important family of extracellular enzymes that catalyse the hydrolysis of high-energy phosphate bonds (HEPBs) in ATP and ADP, thereby modulating many physiological processes and driving life activities. Herein, we report an unexpected discovery that cerium-based metal–organic frameworks (Ce-MOFs) of UiO-66(Ce) have intrinsic apyrase-like activity for ATP/ADP-related physiological processes. The abundant CeIII/CeIV couple sites of Ce-MOFs endow them with the ability to selectively catalyse the hydrolysis of HEPBs of ATP and ADP under physiological conditions. Compared to natural enzymes, they could resist extreme pH and temperature, and present a broad range of working conditions. Based on this finding, a significant inhibitory effect on ADP-induced platelet aggregation was observed upon exposing the platelet-rich plasma (PRP) to the biomimetic UiO-66(Ce) films, prefiguring their wide application potentials in medicine and biotechnology.

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