The first structurally analysed nucleic acid building block containing the Reese protecting group: 2'-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]-β-D-(1'R,2'R,3'R,4'R)-uridine.
The title compound, C21H26FN3O7, is assembled by N-H...O and O-H...O hydrogen bonds into well-separated two-dimensional layers of about 15 Å thickness. The crescent conformation of the molecules is stabilized by weak intramolecular C-H...O and C-H...F hydrogen bonds. The uridine moiety adopts an anti conformation. The ribofuranose ring exists in an envelope conformation. All the endocyclic uracil bonds are shorter than normal single C-N and C-C bonds, and five of them have comparable lengths, which implies a considerable degree of delocalization of the electron density within this ring.
Institute of General and Ecological Chemistry, Lodz University of Technology, ul. Zeromskiego 116, 90-924 Lodz, Poland.
Rafal
R
Kruszynski
Institute of Organic Chemistry, Lodz University of Technology, ul. Zeromskiego 116, 90-924 Lodz, Poland.
Wojciech
W
Czestkowski
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D009696:Nucleic Acids / Q000032:analysis* / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry*
C000600113:2'-O-(1-(2-fluorophenyl)-4-methoxypiperidin-4-yl)-beta-D-(1'R,2'R,3'R,4'R)-uridine; D009696:Nucleic Acids; D014529:Uridine
RNA element; Reese protecting group; crystal structure; hydrogen bonding; natural products; nucleic acid; ribofuranose ring; two-dimensional layers; uracil bonds; uridine