58-61-7

Usage

Uses

Used in Pharmaceutical Industry:
Adenosine is used as an antiarrhythmic and cardiac depressant for the treatment of certain heart conditions. It helps regulate heart rhythm and reduces the workload on the heart.
Used in Cosmetics Industry:
Adenosine is used as an ingredient in anti-wrinkle and skin-smoothing products due to its potential to improve skin texture and appearance.
Used in Biochemical Research:
Adenosine is used as a nucleotide in research and development, playing a vital role in biochemical processes such as energy transfer and signal transduction.
Used in Biotechnology:
Adenosine is used in the study of osteogenic differentiation, as it influences the differentiation of osteoclasts and osteoblasts through its receptors A1R and A2AR, respectively.
Chemical Properties:
Adenosine is a white, crystalline, odorless powder with a mild, saline, or bitter taste. It is quite soluble in hot water and practically insoluble in alcohol. It is formed by isolation following the hydrolysis of yeast nucleic acid.
Brand Names:
Adenocard (Astellas) and Adenoscan (Astellas) are brand names for adenosine-based pharmaceutical products.

Defination

Adenosine is a natural nucleotide, which is the intermediate product of metabolism, chemically 6-amino-9-beta-D-ribofuranosyl-9-H-purine. Adenosine is one of the important active components in the body, helps in cellular energy transfer by forming molecules like adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signaling various pathways and functions in the body by forming signally molecules like cyclic adenosine monophosphate (cAMP).

In the body

▼▲ Adenosine in the body Function Brain Promoting sleep and suppresses arousal acting as a central nervous system depressant. Heart Causing dilation of the coronary blood vessels that Improving blood circulation to the heart; Increasing the diameter of blood vessels in the peripheral organs; Decreasing heart rate Blood Broken down by adenosine deaminase. By taking medicine like Dipyridamole(inhibitor of adenosine deaminase), it can improve blood flow through the coronary blood vessels that supply the heart muscles. Kidneys, lungs and liver In the kidneys adenosine decreases renal blood flow and decrease the production of rennin from the kidneys. In the lungs it causes constriction of airways and in the liver it leads to constriction of blood vessels and increases breakdown of glycogen to form glucose.

Medical uses

Adenosine has a role in the expansion of coronary artery and myocardial contractility, is clinically applied in the treatment of angina, hypertension, cerebrovascular disorders, stroke sequelae, muscular atrophy, etc. It is also given intravenously (by IV) for treating supraventricular tachycardia and Tl myocardial imaging. It is also used for cardiac stress tests. ? Side effects: Since the half-life of Adenosine is less than 10 seconds, its side effects are usually transient. However, side effects are common, and include flushing, headache, chest discomfort, bronchoconstriction, and occasionally hypotension. Hepatic and renal failure and other drugs except dipyridamole seem to have little effect on the action of adenosine. ? ? Adenosine dose

Mechanism of action

Its function is realized through the activation of the adenosine receptor (A receptor). Adenosine activates G protein coupled potassium channels by binding to the A receptor which makes increasing the outflow of K+ and cell membrane hyperpolarization so as to decrease the automaticity in the atrium, sinoatrial node and atrioventricular node. It can also significantly increase the level of cGMP , prolong ERP of the atrioventricular node and slowing of atrioventricular, depress sympathetic nervous or early and delayed after depolarization induced by isoproterenol and then plays an effective role in arrhythmia. This product has not been classified in I~IV anti arrhythmia medicine. Adenosine receptor A1 receptors, which are found in cardiomyocytes and which are responsible for the inhibition of adenylyl cylase activity which lowers cyclic adenosine monophosphate (AMP) results in sinus slowing, increase in AV node conduction delay, and antagonism of the effects of catecholamines; A2 receptors, which are found in endothelial cells and vascular smooth muscle and are responsible for the enhancement of adenylyl cylase activity and increased cyclic AMP which relaxes smooth muscle. Both negative chronotropic and dromotropic effects of adenosine are cyclic AMP independent (direct action) as well cyclic AMP dependent (indirect action).

Biological Activity

Neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes.

Biochem/physiol Actions

Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti?inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

Clinical Use

Adenosine (Adenocard) is an endogenous nucleoside that is a product of the metabolism of adenosine triphosphate. It is used for the rapid termination of supraventricular arrhythmias following rapid bolus dosing. Adenosine is approved for the acute management and termination of supraventricular tachyarrhythmias, including A-V nodal reentrant tachycardia and A-V reciprocating tachycardia. Adenosine may be helpful in the diagnosis of atrial flutter.

Side effects

Adverse reactions to the administration of adenosine are fairly common; however, the short half-life of the drug limits the duration of such events.The most common adverse effects are flushing, chest pain, and dyspnea. Adenosine may induce profound bronchospasm in patients with known reactive airway disease. The mechanism for bronchospasm is unclear, and the effect may last for up to 30 minutes despite the short half-life of the drug.

Drug interactions

Metabolism of adenosine is slowed by dipyridamole, indicating that in patients stabilized on dipyridamole the therapeutically effective dose of adenosine may have to be increased. Methylxanthines antagonize the effects of adenosine via blockade of the adenosine receptors.

Metabolism

It is impossible to study adenosine in classical pharmacokinetic studies, since it is present in various forms in all the cells of the body. An efficient salvage and recycling system exists in the body, primarily in erythrocytes and blood vessel endothelial cells. The halflife in vitro is estimated to be less than 10 seconds, and may be even shorter in vivo.

Purification Methods

Crystallise adenosine from distilled water and dry it at 110o. It has been purified via the picrate, where ethanolic picric acid is added to adenosine and the picrate is filtered off and recrystallised from EtOH. It has m 180-185o(dec). Adenosine is recovered by dissolving 0.4g of the picrate in 80mL of hot H2O, treated with a small quantity of Dowex 1 anion exchange resin in the chloride form, and the resin is filtered off. The filtrate is treated with more resin and filtered again. One equivalent of aqueous NaOH is added to the colourless filtrate which is evaporated to 4mL and cooled to give 0.176g of adenosine m 236o. [Davoll et al. J Chem Soc 967 1948, Davoll & Lowy J Am Chem Soc 73 1650 1951, Beilstein 26 III/IV 3598.]

Precautions

Patients with second- or third-degree A-V block should not receive adenosine. As indicated previously, the use of adenosine in asthmatic patients may exacerbate the asthmatic symptoms.

InChI:InChI=1/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6+,7+,10+/m1/s1

Synthetic route

(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol (35638-82-5) → adenosine (58-61-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 50℃;	100%

triacetyladenosine (7387-57-7) → adenosine (58-61-7)

Conditions	Yield
With lipase A from Aspergillus niger In aq. phosphate buffer; acetonitrile at 25℃; for 0.5h; pH=7; Enzymatic reaction;	99%
With ammonia at 25℃;	83%
With methanol; ammonia

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine (69304-45-6) → adenosine (58-61-7)

Conditions	Yield
With ammonium fluoride In methanol at 60℃; for 3h;	99%
With ammonium fluoride In methanol at 60℃; for 3h; other silyl ethers;	99%

N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (88121-73-7) + methylamine (74-89-5) → 2-(4-nitrophenyl)ethyl N-methylcarbamate + adenosine (58-61-7)

Conditions	Yield
In 1,4-dioxane for 1.5h; Product distribution; Mechanism; Ambient temperature;	A 93% B 99%

5'-O-(p-methoxyphenyldiphenylmethyl)adenosine (51600-11-4) → adenosine (58-61-7)

Conditions	Yield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 0.1h; detritylation;	98%
With hydrogenchloride In water; acetonitrile at 60℃; for 0.25h; pH=Ca. 1; Inert atmosphere;	63 mg

N6-methyladenosine (1867-73-8) → adenosine (58-61-7)

Conditions	Yield
With benzophenone; Selectfluor In water; acetonitrile for 5h; Reagent/catalyst; Inert atmosphere; UV-irradiation;	97%
With Selectfluor; riboflavin In water; acetonitrile at 37℃; under 760.051 Torr; for 2h; Reagent/catalyst; Inert atmosphere; Irradiation;	86%
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Mechanism; Kinetics; Reagent/catalyst; Irradiation; chemoselective reaction;	79%
With dihydrogen peroxide; ammonium bicarbonate at 37℃; for 24h;

5'-O-(triphenylmethyl)adenosine (18048-85-6) → adenosine (58-61-7)

Conditions	Yield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 1.5h; detritylation;	95%
With cerium(IV) triflate; water In acetonitrile at 25℃; for 1.5h;	88%
With chlorine In chloroform at 4℃; for 0.5h;	85%
With sulfuric acid; water; silica gel In acetonitrile at 25℃; for 0.283333h;	82%
With trifluoroacetic acid In water; acetonitrile at 0 - 20℃; for 12h;	36 mg

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-methoxybenzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol (23666-24-2) → adenosine (58-61-7)

Conditions	Yield
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h;	95%

5'-O-dimethoxytrityladenosine (57018-82-3, 81352-25-2) → adenosine (58-61-7)

Conditions	Yield
With K 10 clay In methanol; water for 20h; Ambient temperature;	95%
With cerium(IV) triflate; water In acetonitrile at 25℃; for 0.75h;	95%
With 1,1,1,3',3',3'-hexafluoro-propanol for 1h; Ambient temperature;	87 % Turnov.
Multi-step reaction with 6 steps 1: Et3N; DMAP / CH2Cl2 2: dichloroacetic acid; pyrrole / CH2Cl2 3: 87 percent / 2,4,6-triisopropylbenzenesulfonyl chloride; 3-nitro-1,2,4-1H-triazole; pyridine / 1 h / 20 °C 4: Me3SiCl / acetonitrile / 6 h / 60 °C 5: 0.060 g / aq. NH3 / acetonitrile / 0.08 h / 20 °C 6: CD3CO2D; D2O / 23 °C View Scheme

8-bromoadenosine (2946-39-6) → adenosine (58-61-7)

Conditions	Yield
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol In water at 100℃; for 4h;	94%
With potassium fluoride; N,O-bis-(trimethylsilyl)-acetamide; perhydrodibenzo-18-crown-6 In acetonitrile for 96h; Heating;	36%
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol; 1,1'-azobis(1-cyanocyclohexanenitrile); triethylamine In water at 100℃; for 1h;	94 % Turnov.
Multi-step reaction with 2 steps 1.1: H2SO4; NaNO2; KBr / 3 h / -15 - 20 °C 1.2: H2O / 65 °C 1.3: 0.14 g / aq. NaOH / dimethylsulfoxide / 5 h 2.1: UV-irradiation View Scheme
Multi-step reaction with 3 steps 1: pyridine / 0.5 h 2: sodium naphthalenide / tetrahydrofuran / -60 °C 3: aq. NH3 / methanol / 0.5 h View Scheme

5'-(O-tert-butyldimethylsilyl)adenosine (69530-93-4) → adenosine (58-61-7)

Conditions	Yield
With K 10 clay In methanol; water at 75℃; for 10h;	93%

(2R,3R,4S,5R)-2-(6-(tritylamino)-9H-purin-9-yl)-5-((trityloxy)methyl)tetrahydrofuran-3,4-diol (31085-55-9) → adenosine (58-61-7)

Conditions	Yield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 2h; detritylation;	92%

adenosine 1-oxide (146-92-9, 7013-17-4, 14215-95-3) → adenosine (58-61-7)

Conditions	Yield
With Dimethylphenylsilane In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere;	91%
With GLUTATHIONE for 144h; Product distribution; Mechanism; Ambient temperature; Irradiation; pH 7.0 (phosphate buffer);	60%

5'-(anthraquinon-2-ylmethoxycarbonyl)adenosine (350498-61-2) → adenosine (58-61-7)

Conditions	Yield
With KMOPS buffer In tetrahydrofuran Photolysis;	91%

[9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-carbamic acid 2-nitro-benzyl ester (473910-22-4) → adenosine (58-61-7)

Conditions	Yield
In 1,4-dioxane; water for 1.5h; UV-irradiation;	90%

N6-Benzyladenosine (4294-16-0) → adenosine (58-61-7)

Conditions	Yield
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h;	89%

adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) + uridine (58-96-8) → adenosine (58-61-7)

Conditions	Yield
With Enterobacter gergoviae CECT 875 in agarose In phosphate buffer at 60℃; for 3h; pH=7.0; Enzymatic reaction;	89%
With Citrobacter koseri In aq. phosphate buffer at 60℃; for 1.5h; pH=7; Microbiological reaction;	62%
With Escherichia coli BL21 In phosphate buffer at 60℃; for 1h; pH=7; Enzymatic reaction;

9-(2R,3R,4R,5R)-3,4-bis((tert-butyldiphenylsilyl)oxy)-5-((((tert-butyldiphenylsilyl)oxy)methyl)oxolan-2-yl)-6-chloro-9H-purine → adenosine (58-61-7)

Conditions	Yield
With ammonia at 120 - 130℃; for 24h;	87.2%

adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) + 5-Methyluridine (1463-10-1) → adenosine (58-61-7)

Conditions	Yield
With Enterobacter gergoviae CECT 875 in agarose In phosphate buffer at 60℃; for 2h; pH=7.0; Enzymatic reaction;	84%
With Escherichia coli BL21 In phosphate buffer at 60℃; pH=7; Enzymatic reaction;

2'-O-tosyladenosine (42776-78-3) → adenosine (58-61-7)

Conditions	Yield
With sodium naphthalenide In tetrahydrofuran at -78℃;	82%

C41H37N5O8Si → adenosine (58-61-7)

Conditions	Yield
With ammonia In methanol at 24℃; for 16h;	80.9%

9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine-6-sulfonamide (123002-33-5) → adenosine (58-61-7)

Conditions	Yield
With ammonia In methanol at -5℃; for 5h;	80%

2',3'-isopropylidene adenosine (362-75-4) → adenosine (58-61-7)

Conditions	Yield
With K 10 clay In methanol; water at 75℃; for 55h;	80%
With water at 150℃; for 0.5h; microwave irradiation;	32%
Multi-step reaction with 3 steps 1.1: DMAP / CH2Cl2 / 17 h / 20 °C 1.2: CH2Cl2 / 48 h / 45 °C 2.1: 98 percent / TFA / tetrahydrofuran; H2O / 13 h 3.1: 91 percent / KMOPS buffer / tetrahydrofuran / Photolysis View Scheme
With erbium(III) triflate In water at 120℃; for 0.5h; Microwave irradiation;	88 % Chromat.

2-hydrazinoadenosine (15763-11-8) → adenosine (58-61-7)

Conditions	Yield
With water; oxygen; copper(II) sulfate at 80℃; for 6h; Green chemistry;	79%
With potassium trimethylsilonate In water at 70℃; for 48h; Temperature; Green chemistry;	89 %Spectr.

8-mercaptoadenosine (3001-45-4) → adenosine (58-61-7)

Conditions	Yield
With nitric acid In water at 50℃; for 1h;	79%

N,N-dimethyladenosine (2620-62-4) → adenosine (58-61-7)

Conditions	Yield
With Selectfluor; riboflavin In water; acetonitrile for 7h; Inert atmosphere; UV-irradiation;	78%

N,N-dimethyladenosine (2620-62-4) → N6-methyladenosine (1867-73-8) + adenosine (58-61-7)

Conditions	Yield
With Selectfluor; riboflavin In water; acetonitrile at 37℃; under 760.051 Torr; for 7h; Inert atmosphere; Irradiation;	A 17% B 78%

5'-O-acetyladenosine (2140-25-2) → adenosine (58-61-7)

Conditions	Yield
With methanol; water; triethylamine at 71℃; Microwave irradiation;	75%

N6,2',3',5'-tetra-O-benzoyladenosine (6984-53-8) → adenosine (58-61-7)

Conditions	Yield
With ammonia In methanol at 50℃; for 16h;	74%
With ammonia In methanol at 24℃; for 72h;	62.7%
With ammonia In methanol Substitution;

acetic anhydride (108-24-7) + adenosine (58-61-7) → 6-N-2',3',5'-tri-O-tetraacetyladenosine (7387-58-8, 80007-24-5)

Conditions	Yield
With pyridine at 20℃;	100%
In pyridine for 8h; Heating;	55%
With sodium acetate
Stage #1: acetic anhydride; adenosine With pyridine at 20 - 60℃; Stage #2: With 1H-imidazole; methanol at 20℃;	2.73 g

acetone (67-64-1) + adenosine (58-61-7) → 2',3'-isopropylidene adenosine (362-75-4)

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester at 20℃;	100%
With p-toluenesulfonic acid monohydrate for 3h; Inert atmosphere;	100%
With toluene-4-sulfonic acid at 20℃; for 1h; Inert atmosphere;	99%

adenosine (58-61-7) → Inosine (58-63-9)

Conditions	Yield
With phosphate buffer at 25℃; for 0.666667h; AMP deaminase from Aspergillus sp.;	100%
With calf intestine adenosine deaminase In water at 20℃; for 24h; Enzymatic reaction;	100%
With water; adenosine deaminase for 16h; Enzymatic reaction;	100%

C12H13N7 (406945-71-9) + adenosine (58-61-7) → (2R,3R,4S,5R)-2-(6-Amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-olate1-(2-amino-9H-purin-6-yl)-4-dimethylamino-pyridinium;

Conditions	Yield
In water-d2	100%

adenosine (58-61-7) → 5'-iodo-5'-deoxyadenosine (4099-81-4)

Conditions	Yield
With pyridine; iodine; triphenylphosphine at 20℃; for 2h;	100%
With pyridine; iodine; triphenylphosphine for 2h;	100%
With pyridine; iodine; triphenylphosphine at 0 - 20℃; for 2h;	90%

3C5H13NO*3C9H9NO3 + adenosine (58-61-7) → 3C5H13NO*3C9H9NO3*C10H13N5O4

Conditions	Yield
at 20℃; for 3h;	100%

2,2-dimethoxy-propane (77-76-9) + acetone (67-64-1) + adenosine (58-61-7) → 2',3'-isopropylidene adenosine (362-75-4)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 72h; Inert atmosphere;	100%
Stage #1: 2,2-dimethoxy-propane; acetone; adenosine With d-10-camphorsulphonic acid for 3h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate

N,N-dibutylformamide dimethyl acetal (19449-30-0) + adenosine (58-61-7) → 6-N-(N,N-dibutylformamidine)adenosine (1228304-61-7)

Conditions	Yield
In methanol at 20℃; for 12h;	100%

4-oxopentanoic acid ethyl ester (539-88-8) + adenosine (58-61-7) → ethyl 3-[4-hydroxymethyl-2-methyl-6-(6-oxo-1,6-dihydropurin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]propionate

Conditions	Yield
Stage #1: 4-oxopentanoic acid ethyl ester; adenosine With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; Stage #2: With calf intestine adenosine deaminase In water; glycerol at 20℃; for 72h; Enzymatic reaction;	100%

tert-butylchlorodiphenylsilane (58479-61-1) + adenosine (58-61-7) → (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol (119898-65-6)

Conditions	Yield
With pyridine; dmap at 20℃; for 72h; Inert atmosphere;	99%
With dmap In pyridine at 20℃; for 40h;	98.9%
In pyridine for 24h; Ambient temperature;	80%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + adenosine (58-61-7) → N6-(N,N'-Dimethylaminomethylene)adenosine (17331-15-6)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 1h;	99%
In N,N-dimethyl-formamide at 40℃; for 1h;	66%

adenosine (58-61-7) → [2,8-2H2]-adenosine (82845-88-3)

Conditions	Yield
With hydrogen; water-d2; palladium on activated charcoal at 110℃; for 24h;	99%
With water-d2; palladium on activated charcoal; hydrogen at 110℃; for 24h;	99%
With hydrogen; water-d2; palladium 10% on activated carbon at 110 - 140℃; for 48h; Product distribution / selectivity; Heating / reflux;	74%
With deuterium In water-d2 at 55℃; under 1500.15 Torr; for 36h; Glovebox;

1-Iodonaphthalene (90-14-2) + adenosine (58-61-7) → 8-1-naphthyladenosine (1037298-62-6)

Conditions	Yield
With copper(l) iodide; caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 120℃; for 13h;	99%

diphenyltin(IV) dichloride (1135-99-5) + adenosine (58-61-7) → [SnCl3(C6H5)(C5H2N4(C4H4O(OH)2CH2OH)NH2)2] + triphenyltin chloride (639-58-7)

Conditions	Yield
In methanol refluxing under N2 for 48 h;; removal of volatiles by distn.; residue was washed with ether in portions; ether extract afforded SnClPh3; elem. anal.;;	A 99% B n/a

Rh2(OCOCH3)2(NHCOCF3)2 (499769-85-6) + water (7732-18-5) + adenosine (58-61-7) → [Rh2(acetato)2(trifluoroacetamido)2(adenosine)]*2H2O

Conditions	Yield
In methanol; water addn. of a hot (60°C) soln. of ligand in methanol to a soln. of rhodium complex in methanol at 60°C, standing at room temp.; filtration, air drying; elem. anal.;	99%

tetrakis(μ-acetato)-dirhodium(II)*dimethanol + adenosine (58-61-7) → tetrakis-μ-acetato-dirhodium(II) adenosine adduct

Conditions	Yield
In methanol; water addn. of a hot (60°C) soln. of ligand in methanol to a soln. of rhodium complex in methanol at 60°C, standing at room temp.; filtration, air drying; elem. anal.;	99%

methanol (67-56-1) + tetrakis(μ-trifluoroacetamidato)dirhodium(II) (81988-04-7) + adenosine (58-61-7) → [Rh2(trifluoroacetamido)4(adenosine)]*2CH3OH

Conditions	Yield
In methanol; water addn. of a hot (60°C) soln. of ligand in methanol to a soln. of rhodium complex in methanol at 60°C, standing at room temp.; filtration, air drying; elem. anal.;	99%

benzoyl chloride (98-88-4) + adenosine (58-61-7) → N6,N6,2'-O,3'-O-tetrabenzoyladenosine (58463-04-0)

Conditions	Yield
Stage #1: adenosine With pyridine; tert-butyldimethylsilyl chloride at 0 - 20℃; for 9h; Stage #2: benzoyl chloride at 0 - 20℃; Stage #3: With trifluoroacetic acid In tetrahydrofuran; water at 20℃; for 3h; Time;	99%

ortho-toluoyl chloride (933-88-0) + adenosine (58-61-7) → N6,N6,2',3',5'-penta-O-toluoyladenosine (104557-13-3)

Conditions	Yield
In pyridine for 4h; Ambient temperature;	98%

benzoic acid anhydride (93-97-0) + adenosine (58-61-7) → 2',3',5'-tri-O-benzoyladenosine (51549-15-6)

Conditions	Yield
With pyridine; dmap for 2h; Ambient temperature;	98%
With dmap In various solvent(s) at 50℃; for 2.5h;	92%

adenosine (58-61-7) → 2',3'-dehydroadenosine (2627-64-7, 4336-89-4, 40110-98-3)

Conditions	Yield
With acetoxyisobutyryl bromide In water; acetonitrile at 20℃; for 1h;	98%

Ν,Ν-diisobutylformamide dimethylacetal (50746-36-6) + adenosine (58-61-7) → N6-diisobutylaminomethyleneadenosine

Conditions	Yield
In methanol	97.4%

2,2-dimethoxy-propane (77-76-9) + adenosine (58-61-7) → 2',3'-isopropylidene adenosine (362-75-4)

Conditions	Yield
With methanesulfonic acid In N,N-dimethyl-formamide; acetone at 60℃; for 6h; Inert atmosphere;	96.3%
With Amberlyst 15H+ resin In DMF (N,N-dimethyl-formamide) at 55℃; for 3h;	95%
With Amberlyst 15H+ resin In N,N-dimethyl-formamide at 55℃; for 3h;	95%

benzoyl chloride (98-88-4) + adenosine (58-61-7) → N6,N6,2',3',5'-pentabenzoyl-β-D-adenosine (62374-23-6)

Conditions	Yield
With pyridine at 65℃; for 4h;	96.2%
In pyridine for 20h;	94%
With pyridine at 80℃; for 4h;	82%

Upstream product

• 2004-06-0 6-Chloropurine riboside 
• 342-69-8 6-methylmercaptopurine riboside 
• 84-21-9 adenosine monophosphate 
• 7387-57-7 triacetyladenosine 
• 56-65-5 ATP 
• 75802-60-7 2,8-dichloro-adenosine 
• 18048-85-6 5'-O-(triphenylmethyl)adenosine 
• 28219-91-2 2'-O-(4-methoxytetrahydropyran-4-yl)adenosine 
• 23666-24-2 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-methoxybenzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol 
• 65109-11-7 2',5'-bis-O-(tert-butyldimethylsilyl)adenosine 
• 89455-76-5 (8-2H)adenosine 
• 13241-24-2 2',3'-O-ethoxymethylene-N⁶-dimethylaminomethyleneadenosine 
• 62906-30-3 adenosine 2′:3′-cyclic monophosphate 
• 362-75-4 2',3'-isopropylidene adenosine 

Downstream Products

• 2382-66-3 Cytidin-(3',5')-adenosin 
• 6554-00-3 Phosphoric acid (2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 
• 2140-79-6 2'-O-methyl adenosine 
• 18048-85-6 5'-O-(triphenylmethyl)adenosine 
• 31085-55-9 (2R,3R,4S,5R)-2-(6-(tritylamino)-9H-purin-9-yl)-5-((trityloxy)methyl)tetrahydrofuran-3,4-diol 
• 62374-23-6 N⁶,N⁶,2',3',5'-pentabenzoyl-β-D-adenosine 
• 979-92-0 S-(5'-adenosyl)-L-homocysteine 
• 1053-73-2 3'-phosphoadenosine-5'-phosphate 
• 3805-37-6 adenosine 3',5'-diphosphate 
• 65649-47-0 N⁶,O^2',3',5'-Tetramethyladenosine 
• 7387-57-7 triacetyladenosine 
• 116183-89-2 2',3'-O-(R)-benzylideneadenosine 
• 51549-15-6 2',3',5'-tri-O-benzoyladenosine 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 

Relevant academic research and scientific papers

Escherichia coli Bl21: A useful biocatalyst for the synthesis purine nucleosides

E. coli BL21 cells were able to synthesize several purine nucleosides from pyrimidine ones. Kinetics and yields of this reaction showed a strong dependence on pH, temperature, reagent concentrations and weight of wet cell paste. Yields over 90% were reached in the synthesis of adenosine.

Abiotic synthesis of purine and pyrimidine ribonucleosides in aqueous microdroplets

Aqueous microdroplets (a nucleobase (uracil, adenine, cytosine, or hypoxanthine) are electrosprayed from a capillary at +5 kV into a mass spectrometer at room temperature and 1 atm pressure with 3 mM divalent magnesium ion (Mg2+) as a catalyst. Mass spectra show the formation of ribonucleosides that comprise a four-letter alphabet of RNA with a yield of 2.5% of uridine (U), 2.5% of adenosine (A), 0.7% of cytidine (C), and 1.7% of inosine (I) during the flight time of ～50 μs. In the case of uridine, no catalyst is required. An aqueous solution containing guanine cannot be generated under the same conditions given the extreme insolubility of guanine in water. However, inosine can base pair with cytidine and thus substitute for guanosine. Thus, a full set of ribonucleosides to generate the purine–pyrimidine base pairs A-U and I-C are spontaneously generated in aqueous microdroplets under similar mild conditions.

A secreted enzyme reporter system for MRI

(Figure Presented) Let's see what comes out: An extracellular enzymatic gene-reporter system for magnetic resonance imaging (MRI) yields strong, reversible contrast changes in response to the expression of secreted alkaline phosphatase (SEAP; see picture). Products of SEAP activity were specifically detected using an iron-oxide-based sensor. The contrast agent is not used up by the enzyme, cell delivery is not required, and multimodal detection is possible.

SYNTHESIS OF 2'-5',3'-5' LINKED TRIADENYLATES

2'-5',3'-5' Linked triadenylates have been synthesized by direct bisadenylylation of adenosine 2' and 3' hydroxyls with an adenosine 5'-phosphorochloridite followed by oxidation.

An enzyme-responsive polymeric superamphiphile

Responding to treatment: A superamphiphile is formed between a double-hydrophilic polymer (methoxy-poly(ethylene glycol)-block-poly(L-lysine hydrochloride)) and a natural enzyme-responsive molecule (adenosine 5-triphosphate). The superamphiphile self-assembles into spherical aggregates, which, upon addition of enzymes, disassemble and release loaded molecules (see picture).

Simultaneous High-Resolution Detection of Bioenergetic Molecules using Biomimetic-Receptor Nanopore

A novel artificial receptor, heptakis-[6-deoxy-6-(2-hydroxy-3-trimethylammonion-propyl) amino]-beta-cyclomaltoheptaose, with similar functions of mitochondrial ADP/ATP carrier protein, was synthesized and harbored in the engineered α-HL (M113R)7 nanopore, forming a single-molecule biosensor for sensing bioenergetic molecules and their transformations. The strategy significantly elevates both selectivity and signal-to-noise, which enables simultaneous recognition and detection of ATP, ADP, and AMP by real-time single-molecule measurement.

Cleavage of short oligoribonucleotides by a Zn2+binding multi-nucleating azacrown conjugate

A multi-nucleating azacrown conjugate (5a) consisting of two 3,5-bis(1,5,9-triazacyclododecan-3-yloxymethyl)benzyl groups attached to 1 and 7 sites of cyclen was prepared and tested as an artificial ribonuclease. The conjugate in the presence of five equivalents of zinc nitrate expectedly showed uridine selectivity comparable to that 1,3,5-tris(1,5,9-triazacyclododecan-3-yl)benzene (2), a compound known to bind to two adjacent uridine residues and cleave the intervening phosphodiester bond. 5a was, however, unable to discriminate between two and three adjacent uridine residues, but cleaved oligonucleotides containing a UpU and UpUpU site at a comparable rate, even when present at sub-saturating concentrations.

New nucleoside-based polymeric supports for the solid phase synthesis of ribose-modified nucleoside analogues

New solid supports, linking protected pyrimidine and purine nucleoside derivatives through the nucleobase, have been prepared. The support, incorporating a suitable derivative of 2′-azido, 2′-deoxyuridine, allowed the simple and efficient solid-phase synthesis of ribose-modified nucleoside and nucleic acid analogues, particularly of aminoacyl derivatives of 2′-deoxy, 2′-amino-uridine, following methodologies well established in peptide and oligonucleotide chemistry.

Simple and rapid colorimetric enzyme sensing assays using non-crosslinking gold nanoparticle aggregation

Non-crosslinking gold nanoparticle (AuNP) aggregation induced by the loss (or screen) of surface charges is applied for enzymatic activity sensing and potentially inhibitor screening. The Royal Society of Chemistry.

Utilization of real-time electrospray ionization mass spectrometry to gain further insight into the course of nucleotide degradation by intestinal alkaline phosphatase

RATIONALE Related with its ability to degrade nucleotides, intestinal alkaline phosphatase (iAP) is an important participant in intestinal pH regulation and inflammatory processes. However, its activity has been investigated mainly by using artificial non-nucleotide substrates to enable the utilization of conventional colorimetric methods. To capture the degradation of the physiological nucleotide substrate of the enzyme along with arising intermediates and the final product, the enzymatic assay was adapted to mass spectrometric detection. Therewith, the drawbacks associated with colorimetric methods could be overcome. METHODS Enzymatic activity was comparatively investigated with a conventional colorimetric malachite green method and a single quadrupole mass spectrometer with an electrospray ionization source using the physiological nucleotide substrates ATP, ADP or AMP and three different pH-values in either methodological approach. By this means the enzymatic activity was assessed on the one hand by detecting the phosphate release spectrometrically at defined time points of enzymatic reaction or on the other by continuous monitoring with mass spectrometric detection. RESULTS Adaption of the enzymatic assay to mass spectrometric detection disclosed the entire course of all reaction components - substrate, intermediates and product - resulting from the degradation of substrate, thereby pointing out a stepwise removal of phosphate groups. By calculating enzymatic substrate conversion rates a distinctively slower degradation of AMP compared to ADP or ATP was revealed together with the finding of a substrate competition between ATP and ADP at alkaline pH. CONCLUSIONS The comparison of colorimetric and mass spectrometric methods to elucidate enzyme kinetics and specificity clearly underlines the advantages of mass spectrometric detection for the investigation of complex multi-component enzymatic assays. The entire course of enzymatic substrate degradation was revealed with different nucleotide substrates, thus allowing a specific monitoring of intestinal alkaline phosphatase activity. Copyright 2014 John Wiley & Sons, Ltd. Copyright