The crystal and molecular structure of 5,6-dihydroisocytidine monohydrate, C9H15N3O5.H2O

Kojić‐Prodić, Biserka; Ružić‐Toroš, Ž.; Coffou, E.

doi:10.1107/s0567740876004767

Cited by 12 publications

(2 citation statements)

References 8 publications

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“…The N1-C2 and C2-0? bonds are, respectively, shortened and extended by 0.03 A; a similar trend has been observed in other 5,6-saturated pyrimidines (21,22) and attributed to stronger conjugation of the lone electron pair on N1 with the C2-02 carbonyl group. The pyrimidine ring of I exhibits an approximate half-chair conformation (Figs.…”

Section: Structure Of the Pyrimidine Ringsupporting

confidence: 81%

Characterization of a γ-radiation-induced decomposition product of thymidine. Crystal and molecular structure of the (−)cis(5R,6S) thymidine glycol

Hruska¹,

Sebastian²,

Grand³

et al. 1987

Can. J. Chem.

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X-ray crystallography was used to determine the structure of (−)cis(5R,6S)-5,6-dihydroxy-5,6-dihydrothymidine, a γ-radiation induced product of thymidine. The crystals belong to the orthorhombic space group P212121 and have cell dimensions a = 8.420(1) Å, b = 10.422(1) Å, and 13.552(1) Å. The half-chair pucker of the 5,6-saturated pyrimidine ring is similar to that observed for the isolated base with the cis configuration, and is described by the Cremer–Pople parameters Q = 0.48 Å, θ = 62°, and [Formula: see text]. The conformation about the N-glycosyl bond is anti; the χ angle (−111.6(5)°) lies at one extreme of the range previously seen for nucleosides (−180 to −115°). The pucker 2T1 of the sugar (P = 151.2°; τm = 36.5°) contrasts with the O4′-endo type of pucker seen in 5,6-dihydrothymidine (0T4) and (5S)-5-hydroxy-5,6-dihydrothymidine (0T1). The conformation about the C4′—C5′ bond is gauche+. The solid state structure is similar to that determined in aqueous solution by 1H nmr.

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Section: Structure Of the Pyrimidine Ringsupporting

confidence: 81%

Characterization of a γ-radiation-induced decomposition product of thymidine. Crystal and molecular structure of the (−)cis(5R,6S) thymidine glycol

Hruska¹,

Sebastian²,

Grand³

et al. 1987

Can. J. Chem.

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“…2 H -Deoxy-2 H -(R)-phenylsul®nyluridine (Hata et al, 1991) also adopts a syn conformation, with 1 CN = 61.6 . The dihydro analogue of (Ib), the ribonucleoside 5,6-dihydroisocytidine monohydrate, which also has the amino group at the 2-position, adopts the usual anti conformation, with 1 CN = 107.6 (Kojic-Prodic et al, 1976). The reason for the preference of a syn conformer of (Ib) is a bifurcated hydrogen bond formed between the 2amino group of the base and atoms O4 H and O5 H of the sugar moiety.…”

Section: Commentmentioning

confidence: 99%