3'-O-Acetyl-2'-de-oxy-uridine.

ABSTRACT: In the two independent but very similar mol-ecules of the title compound, C(11)H(14)N(2)O(6), both nucleobase fragments are nearly planar (both within 0.01?Å) while the furan-ose rings exhibit (2)E-endo envelope conformations. In the crystal, the two 3'-O-acetyl-2'-de-oxy-uridine mol-ecules form a pseudosymmetric dimer of two bases connected via two nearly identical resonance-assisted N-H?O hydrogen bonds. The resulting pair is further connected with neighboring pairs via two similar O-H?O bonds involving the only hydroxyl group of the 2'-de-oxy-furan-ose fragment and the remaining carbonyl oxygen of the nucleobase. These inter-actions result in the formation of an infinite 'double band' along the b axis that can be considered as a self-assembled analogue of a polynucleotide mol-ecule with non-canonical Watson-Crick base pairs. The infinite chains of 3'-O-acetyl-2'-de-oxy-uridine pairs are additionally held together by C-H?O inter-actions involving C atoms of the uracyl base and O atoms of carbonyl groups. Only weak C-H?O contacts exist between neighboring chains.

SUBMITTER: Doboszewski B 

PROVIDER: S-EPMC3050423 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature