Syntheses of (2')3'-15N-amino-(2')3'-deoxyguanosine and determination of their pKa values by 15N NMR spectroscopy.
2'-Amino-2'-deoxyguanosine and 3'-amino-3'-deoxyguanosine are valuable probes for investigating the metal ion interactions at the active site of the group I ribozyme. However, these experiments require a thorough understanding of the protonation state of the amino group at a specific pH. Here, we describe the first syntheses of 2'-15N-amino-2'-deoxyadenosine, 2'-15N-amino-2'-deoxyguanosine, and 3'-15N-amino-3'-deoxyguanosine. The 15N-enriched nucleus allows convenient and accurate determination of the amine pKa by 15N NMR.
Dai
Qing
Q
Department of Biochemistry & Molecular Biology, The University of Chicago, 929 East 57th Street, MC 1028, Chicago, Illinois 60637, USA.
Lea
Charles R
CR
Lu
Jun
J
Piccirilli
Joseph A
JA
D001665:Binding Sites; D003849:Deoxyguanosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016337:RNA, Catalytic / Q000737:chemistry
D016337:RNA, Catalytic; D003849:Deoxyguanosine