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• W1978510512 endingPage "1795" @default.
• W1978510512 startingPage "1779" @default.
• W1978510512 abstract "Crystals of 5‐fluorouridine (5FUrd) have unit cell dimensions a = 7.716(1), b = 5.861(2), c = 13.041(1)Å, α = γ = 90°, β = 96.70° (1), space group P21, Z = 2, ρobs = 1.56 gm/c.c and ρcalc = 1574 gm/c.c The crystal structure was determined with diffractometric data and refined to a final reliability index of 0.042 for the observed 2205 reflections (I ≥ 3σ). The nucleoside has the anti conformation [χ = 53.1(4)°] with the furanose ring in the favorite C2′–endo conformation. The conformation across the sugar exocyclic bond is g+, with values of 49.1(4) and − 69.3(4)° for Φθc and Φ∞ respectively. The pseudorotational amplitude τm is 34.5 (2) with a phase angle of 171.6(4)°. The crystal structure is stabilized by a network of N–H…O and O–H…O involving the N3 of the uracil base and the sugar O3′ and O2′ as donors and the O2 and O4 of the uracil base and O3′ oxygen as acceptors respectively. Fluorine is neither involved in the hydrogen bonding nor in the stacking interactions. Our studies of several 5‐fluorinated nucleosides show the following preferred conformational features: 1) the most favored anti conformation for the nucleoside [χ varies from − 20 to + 60°] 2) an inverse correlation between the glycosyl bond distance and the χ angle 3) a wide variation of conformations of the sugar ranging froni C2′–endo through C3′–endo to C4′–exo 4) the preferred g+ across the exocyclic C4′–C5′ bond and 5) no role for the fluorine atom in the hydrogen bonding or base stacking interactions." @default.
• W1978510512 created "2016-06-24" @default.
• W1978510512 creator A5033799263 @default.
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• W1978510512 date "2004-01-01" @default.
• W1978510512 modified "2023-09-27" @default.
• W1978510512 title "Crystal Structure and Conformation of 5‐Fluorouridine: Conformational Preferences for 5‐Fluorinated Pyranosides" @default.
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• W1978510512 doi "https://doi.org/10.1081/ncn-200034052" @default.
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