9-(1,3-Anhydro-beta-D-psicofuranosyl)adenine.
In the structure of the title compound, C11H13N5O4, the glycosidic torsion angle, chi, is -107.1 (2) degrees [nucleic acid nomenclature used throughout the manuscript; IUPAC-IUB Joint Commision on Biochemical Nomenclature (1983). Eur. J. Biochem. 131, 9-15], indicating the anti conformation. The furanosyl ring adopts an N-type sugar pucker with the following pseudorotational parameters: PN = 50.5 (2) degrees and nu max = 34.9 (1) degrees. The conformation around the C5'-C6' bond is ap (gauche,trans; gt; -g), with a torsion angle gamma of 176.28 (19) degrees. The 1',2'-oxetane ring is not planar but folded along C3'...C1', with an angle of 9.6 (1) degrees.
Roivainen
Jarkko
J
Department of Pharmaceutical Chemistry, University of Kuopio, FIN-70211 Kuopio, Finland.
Mikhailopulo
Igor
I
Reuter
Hans
H
Eickmeier
Henning
H
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray / Q000379:methods*; D015224:Dideoxynucleosides / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D006860:Hydrogen Bonding; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry
C517846:9-(1,3-anhydro-beta-D-psicofuranosyl)adenine; D015224:Dideoxynucleosides; D005663:Furans; D009705:Nucleosides; D000225:Adenine