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130-49-4

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130-49-4 Usage

Chemical Properties

colorless or white to yellowish powder

Uses

Adenosine 2′-monophosphate (2′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP. 2′-AMP inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′-AMP is used in the synthesis of a new photoaffinity lable for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase. 2′,3′-cAMP and 2′-AMP represent a new unexplored pathway for adenosine-based cell regulation.

Check Digit Verification of cas no

The CAS Registry Mumber 130-49-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 0 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 130-49:
(5*1)+(4*3)+(3*0)+(2*4)+(1*9)=34
34 % 10 = 4
So 130-49-4 is a valid CAS Registry Number.

130-49-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name adenosine 2'-phosphate

1.2 Other means of identification

Product number -
Other names adenosine 2'-monophosphoric acid

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:130-49-4 SDS

130-49-4Synthetic route

5'-O-(triphenylmethyl)adenosine
18048-85-6

5'-O-(triphenylmethyl)adenosine

pyridine
110-86-1

pyridine

dibenzyl phosphochloridate
538-37-4

dibenzyl phosphochloridate

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
nachfolgende Behandlung mit wss.Essigsaeure und Hydrierung des Reaktionsprodukts an Palladium/Kohle in H2O;
5'-O-(triphenylmethyl)adenosine
18048-85-6

5'-O-(triphenylmethyl)adenosine

dibenzyl phosphochloridate
538-37-4

dibenzyl phosphochloridate

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With pyridine Erwaermen des Reaktionsprodukts mit wss.Essigsaeure und anschliessend Hydrieren an Palladium/Kohle in H2O.;
With pyridine Erwaermen des Reaktionsprodukts mit wss.Essigsaeure und anschliessendes Hydrieren an Palladium/Kohle in H2O;
acetic acid
64-19-7

acetic acid

adenosine monophosphate
84-21-9

adenosine monophosphate

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
entsteht ein Gleichgewichtsgemisch;
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
Zeitlicher Verlauf der Hydrolyse.Hydrolysis;
acetic acid
64-19-7

acetic acid

[2']adenylic acid monobenzyl ester

[2']adenylic acid monobenzyl ester

A

7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

adenosine
58-61-7

adenosine

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With barium dihydroxide; diethyl ether; trichlorophosphate
With barium dihydroxide; diethyl ether; trichlorophosphate
adenylyl-(2'-5')-adenylyl-(2'-5')-2',3'-O-(1-methoxyhexadecylidene)adenosine
121768-18-1

adenylyl-(2'-5')-adenylyl-(2'-5')-2',3'-O-(1-methoxyhexadecylidene)adenosine

A

2',3'-O-(1-methoxyhexadecylidene)adenosine
121768-19-2

2',3'-O-(1-methoxyhexadecylidene)adenosine

B

adenosine monophosphate
84-21-9

adenosine monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With sodium hydroxide In water for 18h;
monoisopropyl adenosine 3'-monophosphate
52278-64-5

monoisopropyl adenosine 3'-monophosphate

A

monoisopropyl adenosine 2'-monophosphate
132803-62-4

monoisopropyl adenosine 2'-monophosphate

B

adenosine monophosphate
84-21-9

adenosine monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

E

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With hydrogenchloride at 89.1℃; Kinetics; Mechanism; Rate constant; various conditions (pH);
monoisopropyl adenosine 2'-monophosphate
132803-62-4

monoisopropyl adenosine 2'-monophosphate

A

monoisopropyl adenosine 3'-monophosphate
52278-64-5

monoisopropyl adenosine 3'-monophosphate

B

adenosine monophosphate
84-21-9

adenosine monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

E

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With hydrogenchloride at 89.1℃; Kinetics; Mechanism; Rate constant; various conditions (pH);
Conditions
ConditionsYield
With hydrogenchloride at 90.1℃; Rate constant;
adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With water; diaminomethane at 50℃; Rate constant; Mechanism; other diamines, hydrolyse of ApA;
With water; ethylenediamine at 50℃; Rate constant;
With water; Trimethylenediamine at 50℃; Rate constant;
adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

C

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With chicken plasma membrane protein In water at 30℃; for 2h; Product distribution; other temperatures;
With 3+ In water at 50℃; Rate constant; Mechanism; pH 7.0, other reagents 3+, 3+, 3+, 3+, 3+; D2O isotope effect;
monomethyl adenosine 3'-monophosphate
69024-48-2

monomethyl adenosine 3'-monophosphate

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

C

monomethyl adenosine 2'-monophosphate
74494-54-5

monomethyl adenosine 2'-monophosphate

E

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With hydrogenchloride at 89.1℃; Kinetics; Mechanism; Rate constant; various conditions (pH);
monomethyl adenosine 2'-monophosphate
74494-54-5

monomethyl adenosine 2'-monophosphate

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

monomethyl adenosine 3'-monophosphate
69024-48-2

monomethyl adenosine 3'-monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

E

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With hydrogenchloride at 89.1℃; Kinetics; Mechanism; Rate constant; various conditions (pH);
adenylyl-(3'-5')-2-deoxyguanosine

adenylyl-(3'-5')-2-deoxyguanosine

A

7-(2-deoxy-β-D-erythro-pentofuranosyl)-1,7-dihydro-6H-purin-6-one
159791-63-6

7-(2-deoxy-β-D-erythro-pentofuranosyl)-1,7-dihydro-6H-purin-6-one

B

adenosine monophosphate
84-21-9

adenosine monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With sodium hydroxide In water at 37℃; for 24h;
adenylyl-(2'-5')-2'-deoxyguanosine

adenylyl-(2'-5')-2'-deoxyguanosine

A

7-(2-deoxy-β-D-erythro-pentofuranosyl)-1,7-dihydro-6H-purin-6-one
159791-63-6

7-(2-deoxy-β-D-erythro-pentofuranosyl)-1,7-dihydro-6H-purin-6-one

B

adenosine monophosphate
84-21-9

adenosine monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With sodium hydroxide In water at 37℃; for 24h;
adenylyl-(3'-5')-guanosine

adenylyl-(3'-5')-guanosine

A

N7-(β-D-Ribofuranosyl)guanin
15373-27-0

N7-(β-D-Ribofuranosyl)guanin

B

adenosine monophosphate
84-21-9

adenosine monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With sodium hydroxide In water at 37℃; for 24h;
adenylyl-(2'-5')-guanosine

adenylyl-(2'-5')-guanosine

A

N7-(β-D-Ribofuranosyl)guanin
15373-27-0

N7-(β-D-Ribofuranosyl)guanin

B

adenosine monophosphate
84-21-9

adenosine monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With sodium hydroxide In water at 37℃; for 24h;
adenyl(3'-5')phophoadenine
2391-46-0, 30066-84-3, 88054-63-1

adenyl(3'-5')phophoadenine

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

C

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With water; thulium(3+) at 30℃; Rate constant; Tris buffer (pH 8); acceleration of hydrolysis by the rare earth metal(III) ions;
With lanthanum(III) perchlorate; HEPES buffer; dihydrogen peroxide In water at 30℃; Rate constant; also without H2O2; other diribonucleotides;
With ethylenediaminetetraacetic acid; Tris biffer; ethylenediamine at 50℃; Product distribution; Rate constant; Mechanism; pH 8, various amines;
adenyl(3'-5')phophoadenine
2391-46-0, 30066-84-3, 88054-63-1

adenyl(3'-5')phophoadenine

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

D

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With Hepes buffer pH 7; tin(IV) chloride; zinc(II) chloride at 50℃; for 3h; Rate constant; Product distribution; var. of catalyst;
With HEPES buffer; ZnCl2-<(2-pyridylmethyl)2NCH2>2CHOH at 50℃; Kinetics; var. conc., pH;
With lanthanum(III) chloride; HEPES buffer; water at 35℃; Rate constant; var. lanthanide-amines complexes;
ApA

ApA

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

C

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With free ligand L; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid In water at 25℃; Rate constant; pH 7.3; also in the presence of CuCl2, MES (pH 6.0);
Phosphoric acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 8-hydroxy-quinolin-2-ylmethyl ester

Phosphoric acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 8-hydroxy-quinolin-2-ylmethyl ester

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With zinc(II) chloride at 30℃; Rate constant; var. metal chlorides;
Phosphoric acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 2-(8-hydroxy-quinolin-2-yl)-ethyl ester

Phosphoric acid (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 2-(8-hydroxy-quinolin-2-yl)-ethyl ester

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With zinc(II) chloride at 30℃; Rate constant; var. metal chloride;
adenosine 3'-phosphate phenyl ester
144828-27-3

adenosine 3'-phosphate phenyl ester

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

C

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

D

phenol
108-95-2

phenol

Conditions
ConditionsYield
With 3+ In water at 50℃; Rate constant; Mechanism; pH 7.0, other reagents 3+, 3+; D2O isotope effect;
adenylyl 3'-5' cytidine
4833-63-0

adenylyl 3'-5' cytidine

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

C

CYTIDINE
65-46-3

CYTIDINE

Conditions
ConditionsYield
With HEPES buffer; water; dinuclear Cu(II) complex 1 at 25℃; pH=7.5; Kinetics; Further Variations:; Catalysts; pH-values; Hydrolysis;
water
7732-18-5

water

adenosine monophosphate
84-21-9

adenosine monophosphate

acidic ion exchanger

acidic ion exchanger

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
Gleichgewichtseinstellung;
O3',O5'-diacetyl-<2'>adenylic acid

O3',O5'-diacetyl-<2'>adenylic acid

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
With ammonia
adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

phosphodiesterase

phosphodiesterase

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

Conditions
ConditionsYield
Phosphodiesterase aus Kaelber-Milz oder aus Rinder-Pankreas;
hydrogenchloride
7647-01-0

hydrogenchloride

adenosine monophosphate
84-21-9

adenosine monophosphate

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

8-bromoadenosine 2'-phosphate
23583-49-5

8-bromoadenosine 2'-phosphate

Conditions
ConditionsYield
With bromine; sodium acetate In water; acetic acid for 3h; Ambient temperature;70%
adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

adenosine 2'-triphosphate, sodium salt

adenosine 2'-triphosphate, sodium salt

Conditions
ConditionsYield
Stage #1: adenosine 2'-monophosphate With triethylamine In N,N-dimethyl-formamide Molecular sieve;
Stage #2: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.416667h;
Stage #3: With pyrophosphate triethylammonium salt In N,N-dimethyl-formamide at 20℃;
17%
phenyldiazomethane
908094-04-2

phenyldiazomethane

adenosine monophosphate
84-21-9

adenosine monophosphate

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

A

[3']adenylic acid monobenzyl ester
5957-04-0

[3']adenylic acid monobenzyl ester

B

[2']adenylic acid monobenzyl ester

[2']adenylic acid monobenzyl ester

Conditions
ConditionsYield
With N,N-dimethyl-formamide
phenyldiazomethane
908094-04-2

phenyldiazomethane

adenosine monophosphate
84-21-9

adenosine monophosphate

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

[2']adenylic acid monobenzyl ester

[2']adenylic acid monobenzyl ester

Conditions
ConditionsYield
With <3'>adenylic acid monobenzyl ester; N,N-dimethyl-formamide
adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

monomethyl adenosine 2'-monophosphate
74494-54-5

monomethyl adenosine 2'-monophosphate

Conditions
ConditionsYield
With diethyl ether; N,N-dimethyl-formamide
acetic acid
64-19-7

acetic acid

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

adenosine monophosphate
84-21-9

adenosine monophosphate

Conditions
ConditionsYield
Produkt:Gleichgewichtsgemisch;
adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

adenosine 2',3'-cyclic monophosphate
634-01-5

adenosine 2',3'-cyclic monophosphate

Conditions
ConditionsYield
With tributyl-amine; chloroformic acid ethyl ester
With pyridine; dicyclohexyl-carbodiimide
With ammonium hydroxide; formamide; dicyclohexyl-carbodiimide
With trifluoroacetic anhydride
adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

A

1-oxy-[3']adenylic acid
51785-74-1

1-oxy-[3']adenylic acid

B

1-oxy-[2']adenylic acid
51785-73-0

1-oxy-[2']adenylic acid

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid
adenosine 2'-monophosphate
130-49-4

adenosine 2'-monophosphate

A

β-D-ribofuranose
36468-53-8

β-D-ribofuranose

B

adenosine monophosphate
84-21-9

adenosine monophosphate

D

adenosine
58-61-7

adenosine

Conditions
ConditionsYield
With hydrogenchloride at 90.1℃; Product distribution; Rate constant; different pH range, various time;

130-49-4Relevant articles and documents

Dinuclear copper(II) complex that hydrolyzes RNA

Young, Mary Jane,Chin, Jik

, p. 10577 - 10578 (1995)

-

Hetero-dinuclear metal complexes for RNA hydrolysis

Kamitani, Jun,Kawahara, Ryuto,Yashiro, Morio,Komiyama, Makoto

, p. 1047 - 1048 (1998)

In the presence of a ligand having two metal-binding sites, Fe(III)/Zn(II) and Fe(III)/Cd(II) combinations hydrolyze adenylyl(3′-5′)adenosine. The notable activities are ascribed to the synergetic cooperation between the two kinds of metal ions in the hetero-dinuclear complexes.

A Stark Contrast to Modern Earth: Phosphate Mineral Transformation and Nucleoside Phosphorylation in an Iron- and Cyanide-Rich Early Earth Scenario

Burcar, Bradley,Casta?eda, Alma,Lago, Jennifer,Daniel, Mischael,Pasek, Matthew A.,Hud, Nicholas V.,Orlando, Thomas M.,Menor-Salván, César

, p. 16981 - 16987 (2019)

Organophosphates were likely an important class of prebiotic molecules. However, their presence on the early Earth is strongly debated because the low availability of phosphate, which is generally assumed to have been sequestered in insoluble calcium and iron minerals, is widely viewed as a major barrier to organophosphate generation. Herein, we demonstrate that cyanide (an essential prebiotic precursor) and urea-based solvents could promote nucleoside phosphorylation by transforming insoluble phosphate minerals in a “warm little pond” scenario into more soluble and reactive species. Our results suggest that cyanide and its derivatives (metal cyanide complexes, urea, ammonium formate, and formamide) were key reagents for the participation of phosphorus in chemical evolution. These results allow us to propose a holistic scenario in which an evaporitic environment could concentrate abiotically formed organics and transform the underlying minerals, allowing significant organic phosphorylation under plausible prebiotic conditions.

-

Brown,Todd

, p. 44,46 (1952)

-

Synergetic Catalysis by Two Non-lanthanide Metal Ions for Hydrolysis of Diribonucleotides

Irisawa, Makoto,Takeda, Naoya,Komiyama, Makoto

, p. 1221 - 1222 (1995)

Adenylyl(3'-5')adenosine and uridylyl(3'-5')uridine are efficiently hydrolysed at pH 7 by bimetallic cooperation of zinc(ii) with tin(iv), indium(iii), iron(iii) or aluminium(iii).

-

Lipkin et al.

, p. 6075,6198,6202 (1959)

-

Rapid hydrolysis of 2',3'-cAMP with a Cu(II) complex: Effect of intramolecular hydrogen bonding on the basicity and reactivity of a metal- bound hydroxide

Wall, Mark,Linkletter, Barry,Williams, Dan,Lebuis, Anne-Marie,Hynes, Rosemary C.,Chin, Jik

, p. 4710 - 4711 (1999)

-

Kinetic Analysis of Diamine-Catalyzed RNA Hydrolysis

Komiyama, Makoto,Yoshinari, Koichi

, p. 2155 - 2160 (1997)

The catalysis of various amines for the hydrolysis of RNA has been kinetically investigated, and the catalytic rate constants for each of the ionic states of these amines are determined. Ethylenediamine and 1,3-propanediamine are highly active under the physiological conditions, mainly because they preferentially take the catalytically active monocationic forms. The catalysis of these diamines is further promoted by the intramolecular acid-base cooperation of the neutral amine and the ammonium ion. In contrast, monoamines overwhelmingly exist at pH 7 as the inactive cations. Potential application of the catalysis by the diamines and the related oligoamines is discussed.

Kinetics and mechanisms for reactions of adenosine 2'- and 3'-monophosphates in aqueous acid: Competition between phosphate migration, dephosphorylation, and depurination

Oivanen,Lonnberg

, p. 2556 - 2560 (1989)

-

THE PREPARATION OF PERMANGANATE-OXIDISED RIBONUCLEIC ACID AND ITS

HOLBROOK,JONES,WELCH

, p. 3998 - 4004 (1965)

-

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

Gillerman, Irina,Fischer, Bilha

, p. 245 - 256 (2011/08/06)

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

Natural occurrence of 2′,5′-linked heteronucleotides in marine sponges

Lopp, Annika,Reintamm, Tonu,Kuusksalu, Anne,Tammiste, Indrek,Pihlak, Arno,Kelve, Merike

experimental part, p. 235 - 254 (2010/10/19)

2′,5′-oligoadenylate synthetases (OAS) as a component of mammalian interferon-induced antiviral enzymatic system catalyze the oligomerization of cellular ATP into 2′,5′-linked oligoadenylates (2-5A). Though vertebrate OASs have been characterized as 2′-nucleotidyl transferases under in vitro conditions, the natural occurrence of 2′,5′-oligonucleotides other than 2-5A has never been demonstrated. Here we have demonstrated that OASs from the marine sponges Thenea muricata and Chondrilla nucula are able to catalyze in vivo synthesis of 2-5A as well as the synthesis of a series 2′,5′-linked heteronucleotides which accompanied high levels of 2′,5′-diadenylates. In dephosphorylated perchloric acid extracts of the sponges, these heteronucleotides were identified as A2′p5′G, A2′p5′U, A2′p5′C, G2′p5′A and G2′p5′U. The natural occurrence of 2′-adenylated NAD+ was also detected. In vitro assays demonstrated that besides ATP, GTP was a good substrate for the sponge OAS, especially for OAS from C. nucula. Pyrimidine nucleotides UTP and CTP were also used as substrates for oligomerization, giving 2′,5′-linked homo-oligomers. These data refer to the substrate specificity of sponge OASs that is remarkably different from that of vertebrate OASs. Further studies of OASs from sponges may help to elucidate evolutionary and functional aspects of OASs as proteins of the nucleotidyltransferase family.

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