title: 1-(beta-D-Erythrofuranosyl)adenosine.
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.
authors.affiliation: Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, USA.
authors.forename: Paul C
authors.initials: PC
authors.lastname: Kline
authors.forename: Hongqiu
authors.initials: H
authors.lastname: Zhao
authors.forename: Bruce C
authors.initials: BC
authors.lastname: Noll
authors.forename: Allen G
authors.initials: AG
authors.lastname: Oliver
authors.forename: Anthony S
authors.initials: AS
authors.lastname: Serianni
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D020029:Base Pairing; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D010430:Pentosyltransferases / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: C549895:1-(erythrofuranosyl)adenosine; C477004:5'-fluorodeoxyadenosine synthase; D010430:Pentosyltransferases; D000241:Adenosine