Comparative Study of the Photoprotolytic Reactions of D-Luciferin and Oxyluciferin

被引：42

作者：

Erez, Yuval ^{[1
]}

Presiado, Itay ^{[1
]}

Gepshtein, Rinat ^{[1
]}

da Silva, Luis Pinto ^{[2
]}

Esteves da Silva, Joaquim C. G. ^{[2
]}

Huppert, Dan ^{[1
]}

机构：

[1] Tel Aviv Univ, Raymond & Beverly Sackler Fac Exact Sci, Sch Chem, IL-69978 Tel Aviv, Israel

[2] Univ Porto, Fac Ciencias, Dept Quim, Ctr Invest Quim, P-4169007 Oporto, Portugal

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2012年 / 116卷 / 28期

基金：

以色列科学基金会;

关键词：

INTERMOLECULAR PROTON-TRANSFER; FIREFLY LUCIFERASE; PHOTINUS-PYRALIS; BIOLUMINESCENCE; COLOR; LIGHT; PH; MODULATION; MECHANISM; DYNAMICS;

D O I：

10.1021/jp301910p

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：

Optical steady-state and time-resolved spectroscopic methods were used to study the photoprotolytic reaction of oxyluciferin, the active bioluminescence chromophore of the firefly's luciferase-catalyzed reaction. We found that like D-luciferin, the substrate of the firefly bioluminescence reaction, oxyluciferin is a photoacid with pK(a)* value of similar to 0.5, whereas the excited-state proton transfer (ESPT) rate coefficient is 2.2 x 10(10) s(-1), which is somewhat slower than that of D-luciferin. The kinetic isotope effect (KIE) on the fluorescence decay of oxyluciferin is 2.5 +/- 0.1, the same value as that of D-luciferin. Both chromophores undergo fluorescence quenching in solutions with a pH value below 3.

引用

页码：7452 / 7461

页数：10

共 45 条

[21] Evidence of ground-state proton-transfer reaction of 3-hydroxyflavone in neutral alcoholic solvents [J].

Mandal, PK ;

Samanta, A .

JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (32) :6334-6339

[22] Firefly Bioluminescence: A Mechanistic Approach of Luciferase Catalyzed Reactions [J].

Marques, Simone M. ;

da Silva, Joaquim C. G. Esteves .

IUBMB LIFE, 2009, 61 (01) :6-17

[23] Fragment molecular orbital investigation of the role of AMP protonation in firefly luciferase pH-sensitivity [J].

Milne, Bruce F. ;

Marques, Miguel A. L. ;

Nogueira, Fernando .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2010, 12 (42) :14285-14293

[24] Sequential proton transfer through water bridges in acid-base reactions [J].

Mohammed, OF ;

Pines, D ;

Dreyer, J ;

Pines, E ;

Nibbering, ETJ .

SCIENCE, 2005, 310 (5745) :83-86

[25] Base-induced solvent switches in acid-base reactions [J].

Mohammed, Omar F. ;

Pines, Dina ;

Nibbering, Erik T. J. ;

Pines, Ehud .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1458-1461

[26] Excited state proton transfer of pyranine in a γ-cyclodextrin cavity [J].

Mondal, SK ;

Sahu, K ;

Sen, P ;

Roy, D ;

Ghosh, S ;

Bhattacharyya, K .

CHEMICAL PHYSICS LETTERS, 2005, 412 (1-3) :228-234

[27] SPECTROSCOPIC PROPERTIES OF FIREFLY LUCIFERIN AND RELATED COMPOUNDS . AN APPROACH TO PRODUCT EMISSION [J].

MORTON, RA ;

HOPKINS, TA ;

SELIGER, HH .

BIOCHEMISTRY, 1969, 8 (04) :1598-&

[28] Red light in chemiluminescence and yellow-green light in bioluminescence:: Color-tuning mechanism of firefly, Photinus pyralis, studied by the symmetry-adapted cluster-configuration interaction method [J].

Nakatani, Naoki ;

Hasegawa, Jun-ya ;

Nakatsuji, Hiroshi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (28) :8756-8765

[29] Spectral-Structural Effects of the Keto-Enol-Enolate and Phenol-Phenolate Equilibria of Oxyluciferin [J].

Naumov, Pance ;

Kochunnoonny, Manoj .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) :11566-11579

[30] Structure and Spectroscopy of Oxyluciferin, the Light Emitter of the Firefly Bioluminescence [J].

Naumov, Pance ;

Ozawa, Yutaka ;

Ohkubo, Kei ;

Fukuzumi, Shunichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (32) :11590-11605

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