7-Azaindole及相似物之水催化激發態質子轉移反應

吳毓心

doi:10.6342/NTU.2014.00364

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7-Azaindole及相似物之水催化激發態質子轉移反應

Water-Catalyzed Excited-State Proton Transfer Reactions in 7-Azaindole and Its Analogues

吳毓心 , Masters　　Advisor：周必泰　　

英文 DOI： 10.6342/NTU.2014.00364

7-azaindole ； pKa ； pKa＊；激發態質子轉移(ESPT) ；互變異構體； 7-azaindole ； pKa ； pKa＊； excited-state proton transfer (ESPT) ； tautomer

Abstract │ Reference (31) │ Altmetrics

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The mechanism of water-catalyzed excited-state proton transfer (ESPT) reaction for 7-azaindole (7AI) has long been investigated, but there are some controversial viewpoints. Recently, owing to the superiority of sensing biowaters in proteins by a 7AI analogue, 2,7-diazatryptophan, it is timely to reinvestigate water-catalyzed ESPT in 7AI and its analogues in an attempt to unify the mechanism. Herein, a series of 7AI analogues and their methylated derivatives were synthesized to carry out a systematic study on pKa, pKa* and the associated fluorescence spectroscopy and dynamics. The results conclude that all 7AI derivatives undergo water catalyzed ESPT in neutral water. However, for those derivatives with electron-donating substituent (including –H) at C(3), following water catalyzed ESPT to form an excited N(7)-H proton-transfer tautomer, T*, rapid protonation takes place to generate an excited cationic (TC*) species that subsequently undergoes a fast deactivation to the N(1)-H normal species in the ground state. Conversely, protonation in T* is prohibited for those derivatives with an electron-withdrawing groups at the C(2) or C(3), or C(2) atom replaced by an electron-withdrawing nitrogen atom (N(2) in e.g., 2,7-diazatryptophan), giving a prominent green T* emission. Additional support is given by the synthesis of the corresponding N(7)-CH3 tautomer species, for which pKa* of the cationic form, i.e., the N(7)-CH3N(1)-H+ species, is measured to be much greater than 7.0 for those with electron-donating C(3) substituents, whereas it is lower than 7.0 upon anchoring electron-withdrawing groups. For 7AI the previously missing T* emission is clearly resolved with peak wavelength at 530 nm in the pH interval of 13.0-14.5.

Reference ( 31 ) 〈TOP〉

(1) Taylor, C. A.; Elbayoumi, M. A.; Kasha, M. Excited-State Two-Proton Tautomerism in Hydrogen-Bonded N-Heterococlic Base Pairs. Proc. Natl. Acad. Sci. U.S.A. 1969, 63, 253.
連結：
(2) Watson, J. D.; Crick, F. H. C. Molecular Structure of Nucleic Acids - a Structure for Deoxyribose Nucleic Acid. Nature 1953, 171, 737.
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(3) Doudney, C. O.; Rinaldi, C. N. Evidence That Ultraviolet Light-Induced DNA-Replication Death of recA Bacteria Is Prevented by Protein-Synthesis in Repair-Proficient Bacteria. Mutat. Res. 1989, 217, 33.
連結：
(4) Ingham, K. C.; Elbayoumi, M. A. Photoinduced Double Proton-Transfer in a Model Hydrogen-Bonded Base Pair - Effects of Temperature and Deuterium Substitution. J. Am. Chem. Soc. 1974, 96, 1674.
連結：
(5) Moog, R. S.; Maroncelli, M. 7-Azaindole in Alcohols - Solvation Dynamics and Proton-Transfer. J. Phys. Chem. 1991, 95, 10359.
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