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5550-12-9 Usage

Identification test

UV absorbance: A 1/50000 sample solution was prepared with 0.01 mol/L hydrochloric acid solution, which had a maximum absorbance at a wavelength of 256 nm ± 2 nm. A250/A260 ratio is at the range of 0.95 to 1.03, and A280/A260 ratio is at the range of 0.63 to 0.71. Ribose test exhibits positive result. Take 3 mL of 0.03% sample solution, add 0.2 mL of the ethanol solution of 10% dihydroxy toluene, and 3 mL 0.1% ammonium ferric sulfate hydrochloric acid (TS-100), heat in water bath for 10 min, the color of the solution should be green. Organic phosphate test is positive. Take 5 mL of 1% sample solution plus 2 mL of magnesium oxide mixture solution (TS-133), there should be no precipitation occurred. Further add 7 mL of nitric acid and boil for 10min, neutralize with sodium hydroxide solution (TS-224) and should exhibit phosphate reaction (IT-26). The sodium salt test was positive (IT-28). Solubility: it is soluble in water, slightly soluble in ethanol but almost insoluble in acetone and ether (OT-42).

Content analysis

Accurately weigh 500 mg of sample and dissolve with 0.01 mol/L hydrochloric acid, and add the volume up to 1000 ml. Take 10 mL of this solution, and then add 0.01mol/L hydrochloric acid to a final volume of 250 ml and mix. Use 0.01mol/L hydrochloric acid as a control, place it in 1 cm cuvette and measure the absorbance A under the wavelength of 260nm and then calculated as follows: Amount (%) = A/289.8 × 250,000/Sample amount (mg) × 100/(100-Moisture (%)) × 100

Toxicity

ADI is not subject to special provision (FAO/WHO, 2001). LD50:10 mg/kg (rat, oral). After chronic test feeding of 0.1% to 1% feed for 6 months, weight and tissue get no abnormal changes. It can be safely used in food products (FDA, §172.530, 2000). EEC-HACSG provides that it should not be used for infant food.

Usage limit

GB 2760-96: all kinds of food, take GMP limit. FAO WHO: luncheon meat, ham, bacon, etc., 500 mg kg (in guanosine), broth and soup, GMP. Standard for Maximum Allowable amount and maximal allowable residue of Food Additives Name of additive??? Food allowed to use it as additive??? Function of additive??? Maximal allowable amount(g/kg)??? Maximal allowable amount(g/kg) 5'-guanylate disodium??? Food??? Food purpose flavor??? The perfume ingredients used in formulating fragrances shall not exceed the maximal allowable amount documented in GB 2760??? 5'-guanylate disodium??? Food??? Flavoring agent??? Apply appropriate amount based on the demand of production except in cases where there is specific rule

Chemical properties

It appears as colorless to white crystalline or crystalline powder, usually containing 7 molecules of crystal water, being odorless, having unique flavor similar to mushrooms. Melting point is not obvious. It undergoes browning under 240 ℃ and decomposition under 250 ℃. It is stable against acid, alkali, salt and heat. It has strong moisture absorption property and is easily soluble in water (25 ℃, 25%). The pH value of its 5% aqueous solution is 7.0 to 8.5, being slightly soluble in ethanol, acetone and ether. Mouse: oral LD50: 10g/kg, ADI does not require special rule(FAO/WHO, 1994).

Uses

Different sources of media describe the Uses of 5550-12-9 differently. You can refer to the following data:
1. Guanylate sodium is allowed flavoring agent allowed at home and abroad, often used together with MSG and sodium inosinate. When mixed for usage, it has multiplication effect on the taste. It can be used for all types of food and should be subject to appropriate use according to production needs. It is mainly used as condiments, being a new generation food by freshener. It is a kind of flavor agent with mushrooms flavor. It is often used in conjunction with sodium glutamate (adding amount is 1%~5%), there is a very significant increase in freshener effect.
2. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
3. Flavor potentiator in foods.Sodium Guanylate is a salt replacement flavor enhancer. Food additive.
4. Guanosine 5'-monophosphate disodium salt is a flavor enhancer which is a crystalline powder, colorless or white, and has characteristic taste. It is soluble in water, sparingly soluble in alcohol, and practically insoluble in ether. It is obtained by chemical synthesis. It is also termed sodium 5-guanylate and disodium guanosine-5-monophosphate.

Preparation

Different sources of media describe the Preparation of 5550-12-9 differently. You can refer to the following data:
1. The production methods of guanylic acid mainly include enzymatic hydrolysis and fermentation method. In the fermentation method, there are two-step method and combination method with biosynthesis and chemical synthesis, two kinds which are of industrial significance. (1) Ribonucleic acid (RNA) hydrolysis method. See the production method of 5'-inosinic acid disodium. (2) Two-step method. Take glucose as the carbon source and ferment with the Bacillus subtilis mutant to obtain the guanosine. The production level was 10.5 g/L. Then guanosine, in pyridine solution, is acidified with phosphorus oxychloride phosphate to obtain guanylate. (3) Biosynthesis and chemical synthesis. At pH=7, apply Bacillus megaterium (No. 336) for fermentation of glucose (8%) for 90 h at pH = 7, producing 15 g/L 5-amino-4-carboxamide nucleoside (AICAr); then extract by ion exchange, followed by concentration and drying to be dissolved in methanol containing NaOH. Add carbon disulfide for co-heating so that it is converted into 2-thioglycoside; It is finally oxidized with hydrogen peroxide; add excess ammonia and heat to obtain guanosine which is further converted to guanylate through phosphorylation.
2. This flavor enhancer is derived from fungal sources.

Chemical Properties

Different sources of media describe the Chemical Properties of 5550-12-9 differently. You can refer to the following data:
1. Disodium guanylate contains approximately seven molecules of water of crystallization. It has a characteristic taste. Disodium guanylate (GMP) is often used in combination with disodium inosinate (IMP) and monosodium glutamate (MSG). These substances are some of the taste principle components in both animal and vegetable foods, and they contribute to a?fundamental?taste?sensation?called?“savory.” The taste intensity differs with the concentration. Although taste quality of IMP or GMP in the presence of MSG is almost similar, GMP provides smoother “fullness” and “thickness” than IMP. The synergistic effect between nucleotides and MSG in cooking has long been empirically established. For example, in traditional Japanese cooking, soup stocks are made by simmering dried tangle (kombu), rich in glutamate (2.26 to 5.73 g/100 g), along with dried bonito (katsuobishi), rich in IMP (0.63 to 1.31 g/100 g) or with a type of dried mushroom, (shiitake) rich in GMP (0.21 g/100 g). Europeans make soup stocks by cooking animal meats rich in IMP or several kinds of mushrooms rich in GMP, along with vegetables containing glutamate (Burdock, 1997)
2. White crystalline powder

Occurrence

Reported found in mushroom (shiitake, enokidake, matsutake, syoro, hatsutake), pork, chicken and whale

Definition

ChEBI: An organic sodium salt that is the disodium salt of GMP.

Taste threshold values

0.0125 g/dL (in water)

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Disodium Guanylate is a flavor enhancer, obtained via chemical synthesis. It is used in combination with monosodium glutamate and disodium inosinate and helps in contributing to a fundamental taste sensation called savory in both animal and vegetable foods.

Biochem/physiol Actions

Guanosine 5′-monophosphate (GMP) is a ribonucleoside monophospate which upon phosphorylation to GTP becomes incorporated into ribonucleic acids (RNAs) by various RNA polymerase(s). Guanosine-5′-monophosphate (GMP) can be used to study modulation of glutamatergic neurotransmission.

Check Digit Verification of cas no

The CAS Registry Mumber 5550-12-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,5 and 0 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 5550-12:
(6*5)+(5*5)+(4*5)+(3*0)+(2*1)+(1*2)=79
79 % 10 = 9
So 5550-12-9 is a valid CAS Registry Number.

5550-12-9 Well-known Company Product Price

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  • TCI America

  • (G0172)  Guanosine 5'-Monophosphate Disodium Salt Hydrate  >98.0%(HPLC)(N)

  • 5550-12-9

  • 25g

  • 790.00CNY

  • Detail
  • TCI America

  • (G0172)  Guanosine 5'-Monophosphate Disodium Salt Hydrate  >98.0%(HPLC)(N)

  • 5550-12-9

  • 100g

  • 1,990.00CNY

  • Detail
  • TCI America

  • (G0173)  Guanylic Acid Sodium Salt (2'-,3'- mixture) from Yeast  

  • 5550-12-9

  • 1g

  • 405.00CNY

  • Detail
  • TCI America

  • (G0173)  Guanylic Acid Sodium Salt (2'-,3'- mixture) from Yeast  

  • 5550-12-9

  • 5g

  • 1,430.00CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1514)  Disodium Guanylate  (pharmaceutical secondary standard; traceable to USP)

  • 5550-12-9

  • PHR1514-1G

  • 1,006.20CNY

  • Detail

5550-12-9SDS

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 Guanosine 5'-monophosphate disodium salt

1.2 Other means of identification

Product number -
Other names Sodium Guanylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives
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:5550-12-9 SDS

5550-12-9Synthetic route

guanosine-5'-phosphoro-(2-aminoimidazole)

guanosine-5'-phosphoro-(2-aminoimidazole)

A

1H-imidazol-2-amine
7720-39-0

1H-imidazol-2-amine

B

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

Conditions
ConditionsYield
With trimethyl phosphite; water; sodium chloride; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid In water-d2 at 25℃; Kinetics;
guanosine-5'-(2-methylimidazol-1-yl phosphate)
80242-42-8

guanosine-5'-(2-methylimidazol-1-yl phosphate)

A

2-methylimidazole
693-98-1

2-methylimidazole

B

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

Conditions
ConditionsYield
With trimethyl phosphite; water; sodium chloride; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid In water-d2 at 25℃; Kinetics;
C10H14N6O10P2(2-)*2Na(1+)

C10H14N6O10P2(2-)*2Na(1+)

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

Conditions
ConditionsYield
With water; zinc(II) cation pH=5.5;
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

5'-guanosine monophosphate
85-32-5

5'-guanosine monophosphate

Conditions
ConditionsYield
With Dowex 50W×8 resin In water at 20℃; for 0.5h;99%
With Dowex 50WX-8 200 mesh, H+
1H-imidazole
288-32-4

1H-imidazole

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

triethylamine
121-44-8

triethylamine

triethylammonium guanosin-5'-yl monophosphate P-imidazolide

triethylammonium guanosin-5'-yl monophosphate P-imidazolide

Conditions
ConditionsYield
With 2,2'-dipyridyldisulphide; triphenylphosphine In N,N-dimethyl-formamide at 20℃;90%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

1-bromomethyl-3-methoxybenzene
874-98-6

1-bromomethyl-3-methoxybenzene

((2R,3S,4R,5R)-5-(2-amino-7-(3-methoxybenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(3-methoxybenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;81%
cisplatin
15663-27-1

cisplatin

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

cis-[Pt(NH3)2(5'-guanosine monophosphateNa2)2]Cl2

cis-[Pt(NH3)2(5'-guanosine monophosphateNa2)2]Cl2

Conditions
ConditionsYield
In water mixture is heated at 50°C for about 3-5 h with stirring; the clear soln. is left overnight at room temp.;; concn. under vacuum; pptn. with acetone, then with ether; white ppt. isfiltered off, washed with acetone, then with ether and dried in air;;75%
In water stirring Pt-complex with 2 equiv. of ligand (room temp., 3 h, in dark);
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

4-chlorobenzyl bromide
622-95-7

4-chlorobenzyl bromide

((2R,3S,4R,5R)-5-(2-amino-7-(4-chlorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(4-chlorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;75%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

2-methylbenzyl bromide
89-92-9

2-methylbenzyl bromide

((2R,3S,4R,5R)-5-(2-amino-7-(2-methylbenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(2-methylbenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;71%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

benzyl bromide
100-39-0

benzyl bromide

((2R,3S,4R,5R)-5-(2-amino-7-benzyl-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-benzyl-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;70%
N-Acetylimidazole
2466-76-4

N-Acetylimidazole

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

2′,3′-di-O-acetyl β-guanosine-5′-phosphate

2′,3′-di-O-acetyl β-guanosine-5′-phosphate

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 4h; pH=8;70%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

guanosine 5′-(2-fluorodiphosphate) disodium salt

guanosine 5′-(2-fluorodiphosphate) disodium salt

Conditions
ConditionsYield
With fluorophosphate imidazolide lithium salt; magnesium chloride In N,N-dimethyl-formamide for 2h;69%
morpholine
110-91-8

morpholine

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

guanosine-5'-monophosphate morpholidate
7390-53-6

guanosine-5'-monophosphate morpholidate

Conditions
ConditionsYield
Stage #1: morpholine; guanosine 5'-monophosphate disodium With Dowex 50W-X8 resin In water
Stage #2: morpholine; dicyclohexyl-carbodiimide In tert-butyl alcohol at 100℃; for 5h; Further stages.;
68%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

2-bromomethylnaphthyl bromide
939-26-4

2-bromomethylnaphthyl bromide

((2R,3S,4R,5R)-5-(2-amino-7-(naphthalen-2-ylmethyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(naphthalen-2-ylmethyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;68%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

1-bromomethyl-2-chlorobenzene
611-17-6

1-bromomethyl-2-chlorobenzene

((2R,3S,4R,5R)-5-(2-amino-7-(2-chlorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(2-chlorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;67%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

2,5-dichlorobenzylbromide
85482-13-9

2,5-dichlorobenzylbromide

((2R,3S,4R,5R)-5-(2-amino-7-(2,5-dichlorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(2,5-dichlorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;64%
4-bromomethylbenzoic Acid
6232-88-8

4-bromomethylbenzoic Acid

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

((2R,3S,4R,5R)-5-(2-amino-7-(4-carboxybenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(4-carboxybenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;62%
cis-{Pt(NH3)2(1-methylimidazole-N3)Cl}NO3

cis-{Pt(NH3)2(1-methylimidazole-N3)Cl}NO3

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

cis-{Pt(NH3)2(1-methylimidazole-N3)(5'-guanosinemonophosphate-N7)} * 4 H2O

cis-{Pt(NH3)2(1-methylimidazole-N3)(5'-guanosinemonophosphate-N7)} * 4 H2O

Conditions
ConditionsYield
With water In water dissolving cis-(Pt(NH3)2(C3H3N2(CH3))Cl)NO3 in H2O, addn. of disodium salt of 5'-guanosinemonophosphate; warming to 50°C for 50 h;; filtering, concg. under reduced pressure; addn. of abs. ethanol (pptn.); elem. anal.;;60%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

((2R,3S,4R,5R)-5-(2-amino-7-(4-fluorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(4-fluorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;56%
hexammine cobalt(III) chloride

hexammine cobalt(III) chloride

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

2Co(NH3)6(3+)*3(O3POCH2(CHCH(OH)CH(OH)CH(C5H2N4O(NH2))O))(2-)*13H2O={Co(NH3)6}2{C10H12N5PO8}3*13H2O

2Co(NH3)6(3+)*3(O3POCH2(CHCH(OH)CH(OH)CH(C5H2N4O(NH2))O))(2-)*13H2O={Co(NH3)6}2{C10H12N5PO8}3*13H2O

Conditions
ConditionsYield
In water Dropwise addn. of Co-complex soln. to soln. of Na2(5'-GMP);; Cooling in a refrigerator, filtn., washing of orange solid (cold H2O), drying in a desiccator, elem. anal.;54%
1-bromomethyl-3-methyl-benzene
620-13-3

1-bromomethyl-3-methyl-benzene

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

((2R,3S,4R,5R)-5-(2-amino-7-(3-methylbenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(3-methylbenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;51%
o-fluorobenzyl bromide
446-48-0

o-fluorobenzyl bromide

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

((2R,3S,4R,5R)-5-(2-amino-7-(2-fluorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(2-fluorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;48%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

1-(bromomethyl)-2-chloro-5-fluorobenzene
81778-09-8

1-(bromomethyl)-2-chloro-5-fluorobenzene

((2R,3S,4R,5R)-5-(2-amino-7-(2-chloro-5-fluorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(2-chloro-5-fluorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;41%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

4-chlorobenzyl bromide
622-95-7

4-chlorobenzyl bromide

trifluoroacetic acid
76-05-1

trifluoroacetic acid

7-(4-chlorobenzyl)guanosine-5'-monophosphate trifluoroacetate

7-(4-chlorobenzyl)guanosine-5'-monophosphate trifluoroacetate

Conditions
ConditionsYield
Stage #1: guanosine 5'-monophosphate disodium; 4-chlorobenzyl bromide In dimethyl sulfoxide for 22h;
Stage #2: trifluoroacetic acid In water; acetonitrile for 0.5h;
38%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

1-bromomethyl-3-nitrobenzene
3958-57-4

1-bromomethyl-3-nitrobenzene

((2R,3S,4R,5R)-5-(2-amino-7-(3-nitrobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(3-nitrobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;37%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

8-trifluoromethylguanosine 5′-monophosphate ammonium salt

8-trifluoromethylguanosine 5′-monophosphate ammonium salt

Conditions
ConditionsYield
Stage #1: guanosine 5'-monophosphate disodium With tert.-butylhydroperoxide In water; acetic acid; dimethyl sulfoxide at 0 - 20℃; for 72h;
Stage #2: With ammonium acetate In acetonitrile pH=5.9;
35%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

1-bromomethyl-3-trifluoromethylbenzene
402-23-3

1-bromomethyl-3-trifluoromethylbenzene

((2R,3S,4R,5R)-5-(2-amino-6-oxo-7-(3-(trifluoromethyl)benzyl)-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-6-oxo-7-(3-(trifluoromethyl)benzyl)-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;34%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

1-bromomethyl-3-chlorobenzene
766-80-3

1-bromomethyl-3-chlorobenzene

((2R,3S,4R,5R)-5-(2-amino-7-(3-chlorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(3-chlorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;33%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

1-(Bromomethyl)-3-fluorobenzene
456-41-7

1-(Bromomethyl)-3-fluorobenzene

((2R,3S,4R,5R)-5-(2-amino-7-(3-fluorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(3-fluorobenzyl)-6-oxo-1H-purin-1-ium-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h;32%
guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

1-(Bromomethyl)-3-fluorobenzene
456-41-7

1-(Bromomethyl)-3-fluorobenzene

((2R,3S,4R,5R)-5-(2-amino-7-(3-fluorobenzyl)-6-oxo-1,6-dihydro-9H-purin-7-ium-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

((2R,3S,4R,5R)-5-(2-amino-7-(3-fluorobenzyl)-6-oxo-1,6-dihydro-9H-purin-7-ium-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 18h; Inert atmosphere;32%
butynediazo acetamide

butynediazo acetamide

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

C16H19N6O9P(2-)

C16H19N6O9P(2-)

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water at 20℃; for 1h;31%
6-amino-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)hexanamide

6-amino-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)hexanamide

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

((2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydro-furan-2-yl)methylhydrogen(6-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)amino)-6-oxohexyl)phosphoramidate

((2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydro-furan-2-yl)methylhydrogen(6-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)amino)-6-oxohexyl)phosphoramidate

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; dimethyl sulfoxide at 25℃; pH=7.2;31%
morpholine
110-91-8

morpholine

guanosine 5'-monophosphate disodium
5550-12-9

guanosine 5'-monophosphate disodium

guanosine-5′-phosphoromorpholidate

guanosine-5′-phosphoromorpholidate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In water; tert-butyl alcohol at 100℃; for 5h; Reagent/catalyst;27%

5550-12-9Downstream Products

5550-12-9Relevant articles and documents

Enhanced nonenzymatic RNA copying with 2-aminoimidazole activated nucleotides

Li, Li,Prywes, Noam,Tam, Chun Pong,Oflaherty, Derek K.,Lelyveld, Victor S.,Izgu, Enver Cagri,Pal, Ayan,Szostak, Jack W.

, p. 1810 - 1813 (2017)

Achieving efficient nonenzymatic replication of RNA is an important step toward the synthesis of self-replicating protocells that may mimic early forms of life. Despite recent progress, the nonenzymatic copying of templates containing mixed sequences remains slow and inefficient. Here we demonstrate that activating nucleotides with 2-aminoimidazole results in superior reaction kinetics and improved yields of primer extension reaction products. This new leaving group significantly accelerates monomer addition as well as trimer-assisted RNA primer extension, allowing efficient copying of a variety of short RNA templates with mixed sequences.

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