5-Fluorouridine 5'-O-β-D-galactopyranoside

Key facts

CAS number

149965-92-4

Purity

98%

Form

Solid

form

Molecular weight

424.33 Da

Molecular formula

C₁₅H₂₁FN₂O₁₁

PubChem

9867013

Nature

Synthetic

Solubility

Soluble in DMSO

Soluble in water

Biochemical name

5'-O-beta-D-Galactosyl-5-fluorouridine

Biological description

Potent anti-metabolite. Acts via thymidylate synthetase inhibition or incorporation into RNA *in vivo*. Analog of 5-fluorouridine. Has galactose conjugated to the active site. Enzymatic or chemical hydrolysis of the galactoside group releases the active anti-metabolite. Useful for cell selection through lacZ specific release of 5-fluorouridine in recombinant cells or tissues.

Canonical smiles

C1=C(C(=O)NC(=O)N1C2C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)F

Isomeric smiles

C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O)O)O)F

InChi

InChI=1S/C15H21FN2O11/c16-4-1-18(15(26)17-12(4)25)13-10(23)8(21)6(28-13)3-27-14-11(24)9(22)7(20)5(2-19)29-14/h1,5-11,13-14,19-24H,2-3H2,(H,17,25,26)/t5-,6-,7+,8-,9+,10-,11-,13-,14-/m1/s1

InChiKey

BTPARJRXLUUYJW-FQKYAJAOSA-N

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxolan-2-yl]-5-fluoropyrimidine-2,4-dione