1-(beta-D-Erythrofuranosyl)adenosine

Acta Crystallogr C. 2010 Apr;66(Pt 4):o215-8. doi: 10.1107/S0108270110008024. Epub 2010 Mar 19.

Abstract

The title compound, also known as beta-erythroadenosine, C(9)H(11)N(5)O(3), (I), a derivative of beta-adenosine, (II), that lacks the C5' exocyclic hydroxymethyl (-CH(2)OH) substituent, crystallizes from hot ethanol with two independent molecules having different conformations, denoted (IA) and (IB). In (IA), the furanose conformation is (O)T(1)-E(1) (C1'-exo, east), with pseudorotational parameters P and tau(m) of 114.4 and 42 degrees, respectively. In contrast, the P and tau(m) values are 170.1 and 46 degrees, respectively, in (IB), consistent with a (2)E-(2)T(3) (C2'-endo, south) conformation. The N-glycoside conformation is syn (+sc) in (IA) and anti (-ac) in (IB). The crystal structure, determined to a resolution of 2.0 A, of a cocrystal of (I) bound to the enzyme 5'-fluorodeoxyadenosine synthase from Streptomyces cattleya shows the furanose ring in a near-ideal (O)E (east) conformation (P = 90 degrees and tau(m) = 42 degrees) and the base in an anti (-ac) conformation.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemistry*
  • Base Pairing
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Pentosyltransferases / chemistry*
  • Stereoisomerism
  • Streptomyces / chemistry*
  • Streptomyces / isolation & purification

Substances

  • 1-(erythrofuranosyl)adenosine
  • 5'-fluorodeoxyadenosine synthase
  • Pentosyltransferases
  • Adenosine