1-(beta-D-Erythrofuranosyl)adenosine.
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.
Kline
Paul C
PC
Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, USA.
Zhao
Hongqiu
H
Noll
Bruce C
BC
Oliver
Allen G
AG
Serianni
Anthony S
AS
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
C549895:1-(erythrofuranosyl)adenosine; C477004:5'-fluorodeoxyadenosine synthase; D010430:Pentosyltransferases; D000241:Adenosine