Evidence of tautomerism in 2-aminopurine from fluorescence lifetime measurements

被引:45
作者
Neely, RK
Magennis, SW
Dryden, DTF
Jones, AC
机构
[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JZ, Midlothian, Scotland
[2] Univ Edinburgh, COSMIC, Edinburgh EH9 3JZ, Midlothian, Scotland
关键词
D O I
10.1021/jp0490857
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The fluorescence decay characteristics of 2-aminopurine (2AP) and 2-aminopurine riboside (2APr) have been investigated as a function of excitation and emission wavelength in aqueous and ethanolic solutions. Global analysis of the decay data shows that 2AP exists as two emitting species, whereas 2APr exists as a single species. This is attributed to 9H/7H tautomerism of 2AP. The proportion of 7H tautomer is estimated to be 20% in ethanol and 40% in water.
引用
收藏
页码:17606 / 17610
页数:5
相关论文
共 22 条
[1]   Ab initio MP2 and DFT calculations of geometry and solution tautomerism of purine and some purine derivatives [J].
Broo, A ;
Holmen, A .
CHEMICAL PHYSICS, 1996, 211 (1-3) :147-161
[2]   A theoretical investigation of the physical reason for the very different luminescence properties of the two isomers adenine and 2-aminopurine [J].
Broo, A .
JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (03) :526-531
[3]   A STUDY OF THE MAJOR GAS-PHASE TAUTOMER OF ADENINE BY MICROWAVE SPECTROSCOPY [J].
BROWN, RD ;
GODFREY, PD ;
MCNAUGHTON, D ;
PIERLOT, AP .
CHEMICAL PHYSICS LETTERS, 1989, 156 (01) :61-63
[4]   C-13 MAGNETIC-RESONANCE .26. QUANTITATIVE-DETERMINATION OF TAUTOMERIC POPULATIONS OF CERTAIN PURINES [J].
CHENON, MT ;
PUGMIRE, RJ ;
GRANT, DM ;
PANZICA, RP ;
TOWNSEND, LB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4636-4642
[5]   Ultrafast excited-state dynamics of adenine and monomethylated adenines in solution: Implications for the nonradiative decay mechanism [J].
Cohen, B ;
Hare, PM ;
Kohler, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13594-13601
[6]   TAUTOMERISM OF PURINES .1. N(7)H REVERSIBLE N(9)H EQUILIBRIUM IN ADENINE [J].
DREYFUS, M ;
DODIN, G ;
BENSAUDE, O ;
DUBOIS, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (09) :2369-2376
[7]  
EASTMAN JW, 1969, BERICH BUNSEN GESELL, V73, P407
[8]   SYNTHESIS AND PROPERTIES OF DEFINED DNA OLIGOMERS CONTAINING BASE MISPAIRS INVOLVING 2-AMINOPURINE [J].
ERITJA, R ;
KAPLAN, BE ;
MHASKAR, D ;
SOWERS, LC ;
PETRUSKA, J ;
GOODMAN, MF .
NUCLEIC ACIDS RESEARCH, 1986, 14 (14) :5869-5884
[9]  
GONELLA NC, 1982, J AM CHEM SOC, V104, P3162
[10]   A DFT study of the water-assisted intramolecular proton transfer in the tautomers of adenine [J].
Gu, JD ;
Leszczynski, J .
JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (15) :2744-2750