Synonym
2'-Deoxy-2'-fluorouridine; 784-71-4; 2'-Fluoro-2'-deoxyuridine; Uridine, 2'-deoxy-2'-fluoro-; 2'-deoxy-2'-fluoro-uridine
IUPAC/Chemical Name
1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
InChi Key
UIYWFOZZIZEEKJ-XVFCMESISA-N
InChi Code
InChI=1S/C9H11FN2O5/c10-6-7(15)4(3-13)17-8(6)12-2-1-5(14)11-9(12)16/h1-2,4,6-8,13,15H,3H2,(H,11,14,16)/t4-,6-,7-,8-/m1/s1
SMILES Code
O=C1NC(C=CN1[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2F)=O
Appearance
To be determined
Purity
>98% (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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
246.19
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: Tuttle JV, Tisdale M, Krenitsky TA. Purine 2'-deoxy-2'-fluororibosides as
antiinfluenza virus agents. J Med Chem. 1993 Jan 8;36(1):119-25. doi:
10.1021/jm00053a015. PMID: 8421277.
2: Karim AS, Weltman JK. Transcription of 2'-deoxy-2'-fluoro-modified and
phosphorothioate-modified RNA templates by HIV-1 reverse transcriptase.
Anticancer Res. 1999 Nov-Dec;19(6B):5419-21. PMID: 10697571.
3: Ueno Y, Yamada Y, Nakanishi M, Kitade Y. A specific substrate-inhibitor, a
2'-deoxy-2'-fluorouridine-containing oligoribonucleotide, against human RNase L.
Bioorg Med Chem. 2003 Nov 17;11(23):5069-73. doi: 10.1016/j.bmc.2003.08.025.
PMID: 14604670.
4: Suck D, Saenger W, Main P, Germain G, Declercq JP. X-ray structure of
3',5'-diacetyl-2'-deoxy-2'-fluorouridine: a pyrimidine nucleoside in the syn
conformation. Biochim Biophys Acta. 1974 Sep 13;361(3):257-65. doi:
10.1016/0005-2787(74)90369-4. PMID: 4279089.
5: Schmidt S, Niemann A, Krynetskaya NF, Oretskaya TS, Metelev VG, Suchomlinov
VV, Shabarova ZA, Cech D. The use of oligonucleotide probes containing
2'-deoxy-2'-fluoronucleosides for regiospecific cleavage of RNA by RNase H from
Escherichia coli. Biochim Biophys Acta. 1992 Feb 28;1130(1):41-6. doi:
10.1016/0167-4781(92)90459-d. PMID: 1371935.
6: Aviñó A, Mazzini S, Ferreira R, Gargallo R, Marquez VE, Eritja R. The effect
on quadruplex stability of North-nucleoside derivatives in the loops of the
thrombin-binding aptamer. Bioorg Med Chem. 2012 Jul 15;20(14):4186-93. doi:
10.1016/j.bmc.2012.06.005. Epub 2012 Jun 9. PMID: 22727781; PMCID: PMC3534854.
7: Brevnov MG, Kubareva EA, Romanova EA, Volkov EM, Karyagina AS, Nikolskaya II,
Gromova ES. Interaction of the MvaI and SsoII methyltransferases with DNAs
altered at the central base pair of the recognition sequence. Gene. 1995 May
19;157(1-2):149-52. doi: 10.1016/0378-1119(94)00738-e. PMID: 7607480.
8: Braasch DA, Jensen S, Liu Y, Kaur K, Arar K, White MA, Corey DR. RNA
interference in mammalian cells by chemically-modified RNA. Biochemistry. 2003
Jul 8;42(26):7967-75. doi: 10.1021/bi0343774. PMID: 12834349.
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