2-Fluoroadenine

white to light yellow crystal powder

2-fluoroadenine is an organofluorine compound that is adenine in which the hydrogen at position 2 (the carbon between the two nitrogens of the pyrimidine ring) is replaced by a fluorine. It has a role as an antineoplastic agent. It is an organofluorine compound and a member of purines.|2-Fluoroadenine is a fluorinated heterocyclic 2-ring compound. 2-fluoroadenine is the base moiety for many carbocyclic and acyclic nucleoside analogues, which may be used in antineoplastic studies.

2-fluoro-6-chloropurine (5, 10 g, 58 mmol) was added to a methanol solution saturated with ammonia (100 mL), heatedThe reaction was allowed to proceed at 50 ° C for 10 hours, cooled and the activated carbon was decolorized. The solvent was removed under reduced pressure to give an oil which was recrystallized from water to give whiteThe solid, which is 2-fluoroadenine (1), yield 86percent. 2.45 kg (16.158 mol) 2, 6-diaminopurine are added to 12.78 kg (48.474 mol) HF/pyridine (70percent by weight) at about 15°C in small, equal portions under vigorous stirring, over about 50 minutes. Thereafter, the reactor content is cooled to - 15°C. 2.17 Kg (18.905 Mol) t-Butyl nitrite are poured in this suspension over about 7 hours, in continuous with a dosing rate of about 5.16 g/min through a pump. At the end of the reaction the reactor temperature is brought to 0°C in about 90 minutes. 110 Litres demineralised H2.54 kg (16.73 mol) 2, 6-diaminopurine is added to 13.24 kg (50.205 Mol) HF/Pyridine (70percent by weight) at about 15°C in small, equal portions under vigorous stirring, over about 50 minutes. Thereafter, the reactor content is cooled to - 15°C. In this suspension, 1.390 kg (19.58 Mol) NaNO2.45 kg (16.158 mol) 2, 6-diaminopurine are added to 12.78 kg (48.474 mol) HF/pyridine (70percent by weight) at about 15° C. in small, equal portions under vigorous stirring, over about 50 minutes. Thereafter, the reactor content is cooled to -15° C. 2.17 Kg (18.905 Mol) t-Butyl nitrite are poured in this suspension over about 7 hours, in continuous with a dosing rate of about 5.16 g/min through a pump. At the end of the reaction the reactor temperature is brought to 0° C. in about 90 minutes. 110 Litres demineralised H2.54 kg (16.73 mol) 2, 6-diaminopurine is added to 13.24 kg (50.205 Mol) HF/Pyridine (70percent by weight) at about 15° C. in small, equal portions under vigorous stirring, over about 50 minutes. Thereafter, the reactor content is cooled to -15° C. In this suspension, 1.390 kg (19.58 Mol) NaNOFor these experiments, SEQ ID NO: 2 was selected as the parent enzyme. Libraries of engineered genes were produced using well-established techniques (e.g., saturation mutagenesis, and recombination of previously identified beneficial mutations). The polypeptides encoded by each gene were produced in HTP as described in Example 1, and the clarified lysates were generated as described in For each enzyme, the clarified cell lysate was diluted 8-fold in 50 mM TEoA, 5 mM MnCF. pH 7.5. Each 100 pL reaction was carried out in 96-well shallow well microtiter plates with 50 % (v/v) diluted lysate, 30 mM compound 4, 36 mM compound 2, 5 g/L PPM (SEQ ID NO: 1004), 100 mM TEoA buffer, and 5.0 mM MnCE at pH 7.5. The plates were heat sealed and incubated at 45C and agitated at 500 RPM in an Infers Thermotron shaker overnight. The plate was removed and quenched by adding 1 volume of 1 : 1 DMSO: 1 M KOH, mixing well until the compounds were dissolved, then diluted lO-fold into 25:75 v:v of acetonitrile: 0.1 M TEoA, pH 7 before analysis. Activity relative to SEQ ID NO: 2 was calculated as the percent conversion of the product formed by the variant enzyme as compared to the percent conversion produced by SEQ ID NO: 2. The percent conversion was quantified by dividing the area of the product peak by the sum of the areas of the substrate and product peaks as determined by HPLC analysis.

A purine nucleoside phosphorylase gene therapy for human malignancy.

Molecular Weight:153.12
XLogP3:-0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Exact Mass:153.04507331
Monoisotopic Mass:153.04507331
Topological Polar Surface Area:80.5
Heavy Atom Count:11
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes