Absolute configuration of Rp-uridine 3',5'-cyclic phosphorothioate.

Abstract:

:Triethylammonium uridine-3',5'-cyclic phosphorothioate crystallizes in space group P2(1)2(1)2(1), a = 7.177(1), b = 13.155(6), c = 21.114(7) A, C15H26N3O7PS, MW 423.4, Z = 4, dx = 1.41g/cm3. The crystal structure was solved by direct methods on the basis of 1493 counter X-ray diffraction data (CuK alpha) and refined to R = 5.1%. The configuration of the thiophosphate group is Rp; conformational parameters are: glycosyl torsion angle anti, -151.9(5) degrees, sugar pucker C(3')-endo with P = 27.3 degrees, vmax = 45.5 degrees, six-membered cycle in chair form. The bond distances in the non-esterified P-S and P-O suggest that the negative charge is distributed between the groups. As illustrated in this and other studies, P-O has a much higher affinity for hydrogen bonds than P-S, indicated here by interactions with triethyl-ammonium N-H and O(2')-H as donors. One additional hydrogen bond N(3)-H---0(4) ties the bases which form a ribbon-like structure. 0(2) and S are not engaged in hydrogen bonds. The triethylammonium ion is two-fold disordered.

journal_name

Nucleic Acids Res

journal_title

Nucleic acids research

authors

Hinrichs W,Steifa M,Saenger W,Eckstein F

doi

10.1093/nar/15.12.4945

subject

Has Abstract

pub_date

1987-06-25 00:00:00

pages

4945-55

issue

12

eissn

0305-1048

issn

1362-4962

journal_volume

15

pub_type

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