Acta Crystallographica, Section C: Crystal Structure Communications 2007-11-01

An unusual syn conformation of 5-formyluracil stabilized by supramolecular interactions.

Gustavo Portalone, Marcello Colapietro

Index: Acta Crystallogr. C 63(Pt 11) , o650-4, (2007)

Full Text: HTML

Abstract

The asymmetric unit of the amino-oxo tautomer of 5-formyluracil (systematic name: 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde), C(5)H(4)N(2)O(3), comprises one planar amino-oxo tautomer, as every atom in the structure lies on a crystallographic mirror plane. At variance with all the previously reported small-molecule crystal structures containing the 5-formyluracil residue, the formyl substituent in the title compound exhibits an unusual syn conformation. The molecules are linked into planar sheets parallel to the bc plane by a combination of six N-H...O and C-H...O hydrogen bonds. Four of the hydrogen bonds are utilized to stabilize the formyl group in the syn conformation.

Related Compounds

  • 5-Formyluracil

Related Articles:

Role of the Escherichia coli and human DNA glycosylases that remove 5-formyluracil from DNA in the prevention of mutations.

2001-03-01

[J. Radiat. Res. 42(1) , 11-9, (2001)]

Repair of the mutagenic DNA oxidation product, 5-formyluracil.

2003-02-03

[DNA Repair (Amst.) 2(2) , 199-210, (2003)]

Nucleotide excision repair of 5-formyluracil in vitro is enhanced by the presence of mismatched bases.

2004-03-16

[Biochemistry 43(10) , 2682-7, (2004)]

Mammalian 5-formyluracil-DNA glycosylase. 2. Role of SMUG1 uracil-DNA glycosylase in repair of 5-formyluracil and other oxidized and deaminated base lesions.

2003-05-06

[Biochemistry 42(17) , 5003-12, (2003)]

Induction of T --> G and T --> A transversions by 5-formyluracil in mammalian cells.

2002-01-15

[Mutat. Res. 513(1-2) , 213-22, (2002)]

More Articles...