61-19-8

Basic information

• Product Name: Adenosine 5'-monophosphate
• Synonyms: a5mp;adenosine,mono(dihydrogenphosphate)(ester);adenosine5’-phosphate;adenovite;adenyl;amp(nucleotide);amp[nucleotide];cardiomone
• CAS NO: 61-19-8
• Molecular Formula: C₁₀H₁₄N₅O₇P
• Molecular Weight: 347.22
• EINECS: 200-500-0
• Product Categories: Pharmaceutical Intermediates;Organic acids;Heterocyclic Compounds;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Nucleotides and their analogs;Nucleic acids;ZADITOR;BEAUTY PEPTIDES;Inhibitors
• Mol File: 61-19-8.mol
• Article Data: 137

Chemical Properties

• Melting Point: 178-185 °C
• Boiling Point: 798.518 °C at 760 mmHg
• Flash Point: 436.728 °C
• Appearance: Colorless to white/Crystalline Powder
• Density: 2.32 g/cm³
• Storage Temp.: −20°C
• Solubility: H2O: with addition of mild alkalisoluble
• PKA: 3.8, 6.2(at 25℃)
• Water Solubility: Soluble in water.
• Merck: 14,158
• CAS DataBase Reference: Adenosine 5'-monophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine 5'-monophosphate(61-19-8)
• EPA Substance Registry System: Adenosine 5'-monophosphate(61-19-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: AU7480500
• TSCA: Yes
• Hazardous Substances Data: 61-19-8(Hazardous Substances Data)

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.

Synthetic route

5,6-dimethyl-1H-benzotriazole adenine dinucleotide ammonium salt → 5,6-dimethyl-1H-benzotriazole mononucleotide ammonium salt (123499-60-5) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) → 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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 mononucleotide ammonium salt (123499-59-2) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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 mononucleotide ammonium salt (123499-62-7) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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 mononucleotide ammonium salt (123499-58-1) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) → 5'-adenosine monophosphate (61-19-8) + adenosine 5'-phosphorofluoride (19375-33-8)

Conditions	Yield
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 mononucleotide ammonium salt (123499-61-6) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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-azaadenosine monophosphate ammonium salt (123499-63-8) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
With phosphodiesterase; tris hydrochloride; magnesium chloride In water at 37℃; for 6h; pH: 9.0;	A 87% B n/a

adenosine (58-61-7) → 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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 → 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
With 1,4-dioxane; ammonium hydroxide at 20℃; for 60h;	85%

D-luciferyl adenylate → 4-hydroxyluciferin + 4-hydroxyluciferyl adenylate + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) → 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
With Nafion 125; lithium perchlorate In N,N-dimethyl-formamide; acetonitrile electrolysis;	80%

D-luciferyl adenylate → 4-hydroxyluciferin + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) + ATP (56-65-5) + coenzyme A (85-61-0) → 3-oxo-23,24-bisnorchol-4-en-22-oyl-coenzyme A (1380518-01-3) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) + N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate (24558-92-7) + thymidine 5'-phosphate sodium salt (33430-62-5, 61240-13-9, 75652-49-2, 85597-60-0) → P1-(adenosin-5'-yl)-P2-(thymidin-5'''-yl) bis(triethylammonium) salt + P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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

disodium adenosine-5' triphosphate (606-67-7, 987-65-5, 4691-96-7, 15237-44-2, 20978-32-9, 71997-34-7, 71997-37-0, 71997-53-0, 71997-56-3) → 5'-adenosine monophosphate (61-19-8) + adenosine 5'-diphosphate (58-64-0)

Conditions	Yield
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) + triethylamine carbonate (15715-58-9) + N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate (24558-92-7) → P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt + 0.2CH2O3*1.2C6H15N*C21H27N7O14P2 + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) + N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate (24558-92-7) + adenosine 5'-triphosphate disodium salt → P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt + 0.6CH2O3*4.6C6H15N*C20H28N10O19P4 + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) + Adenosine 5'<(S)α-thio>diphosphate (59286-20-3) → 5'-adenosine monophosphate (61-19-8) + adenosine 5'-diphosphate (58-64-0)

Conditions	Yield
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) + N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate (24558-92-7) + ADP*H1.6*Na1.4 → P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt + 1.5CH2O3*4.5C6H15N*C20H27N10O16P3 + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) + ribose-5-monophosphate barium salt (24325-23-3, 108321-98-8) + N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate (24558-92-7) → P1-(adenosin-5'-yl)-P2-(ribos-5''-yl) bis(triethylammonium) salt + P1,P2-di(adenosin-5'-yl)diphosphate bis(triethylammonium) salt + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) → acetaldehyde (75-07-0) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) → 8-(4-bromophenyl)adenine (77071-04-6) + 5'-adenosine monophosphate (61-19-8)

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

ATP (56-65-5) → 5'-adenosine monophosphate (61-19-8) + adenosine 5'-phosphorofluoride (19375-33-8)

Conditions	Yield
With water; sodium fluoride at 25℃; pH=5.5; Kinetics; pH-value;	A 8.6% B 1.8%

cAMP (60-92-4) → adenosine monophosphate (84-21-9) + 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) + [5']inosinic acid (21214-07-3) → 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
Biosynthese;

[5']inosinic acid (21214-07-3) → 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
enzymatische Ueberfuehrung;

2',3'-di-O-acetyladenosine (29886-19-9) → 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
ueber mehrere Stufen;

2',3'-Isopropylidene-5'-AMP (20408-44-0) → 5'-adenosine monophosphate (61-19-8)

Conditions	Yield
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) + 5'-adenosine monophosphate (61-19-8) → N6-Etheno-AMP (37482-16-9)

Conditions	Yield
With sodium acetate In water at 37℃; for 12h;	99%
In aq. phosphate buffer at 100℃; for 0.25h; Temperature;

morpholine (110-91-8) + 5'-adenosine monophosphate (61-19-8) → adenosine 5'-phosphoromorpholidate sodium salt (95314-00-4)

Conditions	Yield
With 2,2'-dipyridyldisulphide; triphenylphosphine; sodium iodide In dimethyl sulfoxide for 0.666667h; Ambient temperature;	98%

5'-adenosine monophosphate (61-19-8) + p-toluenesulfonyl chloride (98-59-9) → O2'-(toluene-4-sulfonyl)-[5']adenylic acid (28220-12-4)

Conditions	Yield
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) + 5'-adenosine monophosphate (61-19-8) → adenosine 5'-[sodium (2-methyl-1H-imidazol-1-yl)phosphonate]

Conditions	Yield
With 2,2'-dipyridyldisulphide; triethylamine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 2h; Condensation;	92%

benzaldehyde (100-52-7) + 5'-adenosine monophosphate (61-19-8) → 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	Yield
In trifluoroacetic acid at 0 - 5℃; for 7h;	92%

methyl (2S)-pyrrolidine carboxylate (2577-48-2) + 5'-adenosine monophosphate (61-19-8) → prolinyladenosine-5'-monophosphate methylester

Conditions	Yield
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) + 5'-adenosine monophosphate (61-19-8) → C14H17N7O6P(1-)

Conditions	Yield
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) + 5'-adenosine monophosphate (61-19-8) → adenosine 5'-monophosphate morpholidate (7331-13-7)

Conditions	Yield
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 + 5'-adenosine monophosphate (61-19-8) → adenosine 5'-phosphoric di-n-butylphosphinothioic anhydride (57816-25-8)

Conditions	Yield
	90%

cis-(N,N-dimethyl-ethylenediamine)diaquaplatinum(II) (41575-66-0) + 5'-adenosine monophosphate (61-19-8) → 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)

Conditions	Yield
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) + 5'-adenosine monophosphate (61-19-8) + dicyclohexyl-carbodiimide (538-75-0) → N,N'-dicyclohexyl-4-morpholinecarboxamidinium salt of adenosine-5'-phosphoromorpholidate (24558-92-7)

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

Upstream product

• 60-92-4 cAMP 
• 56-84-8 L-Aspartic acid 
• 21214-07-3 [5']inosinic acid 
• 29886-19-9 2',3'-di-O-acetyladenosine 
• 20408-44-0 2',3'-Isopropylidene-5'-AMP 
• 64-19-7 acetic acid 
• 56-65-5 ATP 
• 10343-04-1 O^2',O^3'-isopropylidene-[5']adenylic acid dibenzyl ester 
• 58-61-7 adenosine 
• 65459-08-7 1-[O⁵-(2-adenosin-5'-yloxy-1,2-dihydroxy-phosphoryl)-β-D-ribofuranosyl]-4-imino-1,4-dihydro-pyridine-3-carboxylic acid 
• 30802-00-7 hydroxycinnamoyl-S-CoA 
• 55062-28-7 2′,3′-di-O-acetyl β-adenosine-5′-phosphate 
• 506-68-3 bromocyane 
• 59286-20-3 Adenosine 5'<(S)α-thio>diphosphate 

Downstream Products

• 68134-83-8 Phosphoric acid mono-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester; compound with N,N'-dicyclohexyl-morpholine-4-carboxamidine 
• 80680-28-0 <2-13C>-adenosine 5'-monophosphate 
• 79982-46-0 6-<3-(4-sulfophenyl)-2-triazen-1-yl>purine ribonucleoside 5'-phosphate 
• 77079-60-8 C₁₇H₂₀N₇O₇P 
• 37482-16-9 1,N⁶-ethenoadenosine 5'-monophosphate 
• 77079-59-5 C₁₆H₁₈N₇O₇P 
• 83285-83-0 Tiazofurin adenine dinucleotide 
• 77079-61-9 C₁₆H₁₇BrN₇O₇P 
• 77079-62-0 C₁₆H₁₈N₇O₁₀PS 
• 61-19-8 Phosphoric acid mono-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester 
• 25030-04-0 8-hydroxyadenonine 5'-monophosphate 
• 5959-90-0 Diadenosine triphosphate 
• 4527-92-8 O^{2'_,O3'_{-hydroxyphosphoryl-O}5'}-phosphono-adenosine 
• 1053-73-2 3'-phosphoadenosine-5'-phosphate 

Relevant articles and documents

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

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

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

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.