The Crystal and Molecular Structure of a Derivative of 1,N6-Ethenoadenosine Hydrochloride. Dimensions and Molecular Interactions of the Fluorescent ϵ-Adenosine (ϵ Ado) System

Andrew H.J. Wang, Laurence G. Dammann, Jorge R. Barrio, Iain C. Paul

Research output: Contribution to journalArticlepeer-review

Abstract

The crystal structure of 7-ethyl-3-β-D-ribofuranosylimidazo[2,1-i]purine hydrochloride monohydrate (3) has been determined both to establish the direction of addition of chloroacetaldehyde to adenine in the preparation of ϵ-adenine derivatives and to probe the molecular interactions of the highly fluorescent e-adenosine derivative. The crystals of 3 are monoclinic, with a = 12.952 (3), b = 6.667 (2), and c = 9.679 (2) Å, and β = 101° 34′ (1′). There are two molecules of C14H18N5O4+Cl-·H2O in the space group P21. The structure has been refined to an R factor of 0.043 in 1373 nonzero reflections. The entire ϵ-adenine moiety is near-planar with a maximum deviation of 0.028 Å among the ring atoms. There are some minor differences in bond lengths in the adenine residue in 3 when compared to unbridged adenine rings, but the greatest differences involve the exocyclic angles at C(6). The arrangement about the glycosyl bond is syn (χCN = −109.1°) and the ribose ring exists in the C(2′) endo-C(1′) exo conformation. The C(4′)-C(5′)exocyclic bond is in the trans-gauche arrangement. The N-H bond in the base, all three O-H bonds in the sugar, and the water molecules are involved in hydrogen bonding in the monohydrate. The crystal can be divided into successive regions (in the a direction) of polar and nonpolar character. In the nonpolar regions, there are infinite stacks (in the b direction) of ϵ-adenine rings, each of which overlap considerably with their neighbors with alternate ring-ring separations of 3.344 and 3.324 Å. These overlaps are compared with those found in related molecules.

Original languageEnglish
Pages (from-to)1205-1213
Number of pages9
JournalJournal of the American Chemical Society
Volume96
Issue number4
DOIs
Publication statusPublished - Feb 1 1974
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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