2-Fluoroadenosine | CAS# 146-78-1 | Nucleosides

MedKoo Cat#: 122475 | Name: 2-Fluoroadenosine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

2-Fluoroadenosine is a nucleoside that has shown high resistance to the enzyme cyclase.

Chemical Structure

2-Fluoroadenosine

CAS#146-78-1

Theoretical Analysis

MedKoo Cat#: 122475

Name: 2-Fluoroadenosine

CAS#: 146-78-1

Chemical Formula: C10H12FN5O4

Exact Mass: 285.0873

Molecular Weight: 285.24

Elemental Analysis: C, 42.11; H, 4.24; F, 6.66; N, 24.55; O, 22.44

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 650.00	2 Weeks
10g	USD 950.00	2 Weeks

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Synonym

2-Fluoroadenosine; (2R,3R,4S,5R)-2-(6-Amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; ADENOSINE, 2-FLUORO-; 6-Amino-2-fluoro-9-beta-D-ribofuranosylpurine

IUPAC/Chemical Name

(2R,3R,4S,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

InChi Key

HBUBKKRHXORPQB-UUOKFMHZSA-N

InChi Code

InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

SMILES Code

OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(F)=NC(N)=C3N=C2)O1

Appearance

To be determined

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 285.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Ye S, Rezende MM, Deng WP, Herbert B, Daly JW, Johnson RA, Kirk KL. Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase. J Med Chem. 2004 Feb 26;47(5):1207-13. doi: 10.1021/jm0303599. PMID: 14971900. 2: Zimmerman TP, Rideout JL, Wolberg G, Duncan GS, Elion GB. 2-Fluoroadenosine 3':5'-monophosphate. A metabolite of 2-fluoroadenosine in mouse cytotoxic lymphocytes. J Biol Chem. 1976 Nov 10;251(21):6757-66. PMID: 185217. 3: Ye S, Rezende MM, Deng WP, Kirk KL. Convenient synthesis of 2'-deoxy-2-fluoroadenosine from 2-fluoroadenine. Nucleosides Nucleotides Nucleic Acids. 2003 Oct;22(10):1899-905. doi: 10.1081/NCN-120025237. PMID: 14609229. 4: PITTILLO RF, MONCRIEF C, BROCKMAN RW, CHAMBERS P. ANTIMICROBIAL ACTIVITY OF 2-FLUOROADENOSINE AND 2-FLUOROADENINE. Antimicrob Agents Chemother (Bethesda). 1964;10:474-84. PMID: 14287979. 5: Ishihama A, Enami M, Nishijima Y, Fukui T, Ohtsuka E, Ikehara M. 2'-Deoxy-2'-azidoadenosine triphosphate and 2'-deoxy-2'-fluoroadenosine triphosphate as substrates and inhibitors for Escherichia coli DNA-dependent RNA polymerase. J Biochem. 1980 Mar;87(3):825-30. doi: 10.1093/oxfordjournals.jbchem.a132812. PMID: 6156150. 6: Berzin VB, Dorofeeva EV, Leonov VN, Miroshnikova AI. [The preparative method for 2-fluoroadenosine synthesis]. Bioorg Khim. 2009 Mar-Apr;35(2):210-4. Russian. doi: 10.1134/s1068162009020071. PMID: 19537172. 7: Dickinson MJ, Holly FW, Walton E, Zimmerman M. 3'-deoxynucleosides. V. 3'-Deoxy-2-fluoroadenosine. J Med Chem. 1967 Nov;10(6):1165-6. doi: 10.1021/jm00318a042. PMID: 6056051. 8: Decking UK, Alves C, Spahr R, Schrader J. 2-Fluoroadenosine uptake by erythrocytes and endothelial cells studied by 19F-NMR. Am J Physiol. 1994 Apr;266(4 Pt 2):H1596-603. doi: 10.1152/ajpheart.1994.266.4.H1596. PMID: 8184939. 9: Ohrui H, Kohgo S, Hayakawa H, Kodama E, Matsuoka M, Nakata T, Mitsuya H. 2'-deoxy-4'-C-ethynyl-2-fluoroadenosine: a nucleoside reverse transcriptase inhibitor with highly potent activity against wide spectrum of HIV-1 strains, favorable toxic profiles, and stability in plasma. Nucleosides Nucleotides Nucleic Acids. 2007;26(10-12):1543-6. doi: 10.1080/15257770701545218. PMID: 18066823. 10: Ohrui H. 2'-deoxy-4'-C-ethynyl-2-fluoroadenosine, a nucleoside reverse transcriptase inhibitor, is highly potent against all human immunodeficiency viruses type 1 and has low toxicity. Chem Rec. 2006;6(3):133-43. doi: 10.1002/tcr.20078. PMID: 16795005. 11: Ohrui H, Kohgo S, Hayakawa H, Kodama E, Matsuoka M, Nakata T, Mitsuya H. 2'-Deoxy-4'-C-ethynyl-2-fluoroadenosine: a nucleoside reverse transcriptase inhibitor with highly potent activity against all HIV-1 strains, favorable toxic profiles and stability in plasma. Nucleic Acids Symp Ser (Oxf). 2006;(50):1-2. doi: 10.1093/nass/nrl001. PMID: 17150787. 12: Agarwal KC, Parks RE Jr. Synergistic inhibition of platelet aggregation by forskolin plus PGE1 or 2-fluoroadenosine: effects of 2',5'-dideoxyadenosine and 5'-methylthioadenosine. Biochem Pharmacol. 1982 Nov 15;31(22):3713-6. doi: 10.1016/0006-2952(82)90608-6. PMID: 6983882. 13: Kayushin AL, Tokunova JA, Fateev IV, Arnautova AO, Berzina MY, Paramonov AS, Lutonina OI, Dorofeeva EV, Antonov KV, Esipov RS, Mikhailopulo IA, Miroshnikov AI, Konstantinova ID. Radical Dehalogenation and Purine Nucleoside Phosphorylase E. coli: How Does an Admixture of 2',3'-Anhydroinosine Hinder 2-fluoro- cordycepin Synthesis. Biomolecules. 2021 Apr 7;11(4):539. doi: 10.3390/biom11040539. PMID: 33917025; PMCID: PMC8067715. 14: Gao ZG, Jacobson KA. Partial agonists for A(3) adenosine receptors. Curr Top Med Chem. 2004;4(8):855-62. doi: 10.2174/1568026043450989. PMID: 15078216; PMCID: PMC3425644.