REACTIVITY TOWARD SINGLET OXYGEN OF A 7,8-DIHYDRO-8-OXOGUANOSINE (8-HYDROXYGUANOSINE) FORMED BY PHOTOOXIDATION OF A GUANOSINE DERIVATIVE

被引：126

作者：

SHEU, C ^{[1
]}

FOOTE, CS ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 24期

关键词：

D O I：

10.1021/ja00129a004

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total quenching (k(r) + k(q)) and chemical reaction rates (k(r)) for the removal of singlet oxygen by 2,3',5'-tris((tert-butyldimethylsilyl)oxy)guanos (1) and its oxidation product, 2',3',5'-tris((tert-butyldimethylsilyl)oxy)-7,8-dihydro-8-oxoguanosine (2), were determined by the time-resolved infrared luminescence technique and competition experiments, respectively. Compound 2 is two orders of magnitude more reactive with singlet oxygen than 1. A mechanism for the formation of 2 from 1 with singlet oxygen is proposed.

引用

下载

页码：6439 / 6442

页数：4

共 25 条

[1] Reactivity toward singlet oxygen of a 7,8-dihydro-8-oxoguanosine ('8-hydroxyguanosine') formed by photooxidation of a guanosine derivative
J Am Chem Soc, 24 (6439):
[2] PHOTOSENSITIZED OXYGENATION OF A 7,8-DIHYDRO-8-OXOGUANOSINE DERIVATIVE - FORMATION OF DIOXETANE AND HYDROPEROXIDE INTERMEDIATES
SHEU, CM
FOOTE, CS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) : 474 - 477
[3] Photosensitized oxygenation of a 7,8-dihydro-8-oxoguanosine derivative. Formation of dioxetane and hydroperoxide intermediates
Sheu, C.
Foote, C.S.
Journal of the American Chemical Society, 1995, 117 (01):
[4] Photosensitized oxygenation of a 7,8-dihydro-8-oxoguanosine derivative. Formation of dioxetane and hydroperoxide intermediates
Sheu, C.
Foote, C.S.
Journal of the American Chemical Society, 1995, 117 (16)
[5] An Organometallic Inhibitor for the Human Repair Enzyme 7,8-Dihydro-8-oxoguanosine Triphosphatase
Streib, Manuel
Kraeling, Katja
Richter, Kristin
Xie, Xiulan
Steuber, Holger
Meggers, Eric
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) : 305 - 309
[6] 7,8-Dihydro-8-oxoguanosine Lesions Inhibit the Theophylline Aptamer or Change Its Selectivity
Kiggins, Courtney
Skinner, Austin
Resendiz, Marino J. E.
CHEMBIOCHEM, 2020, 21 (09) : 1347 - 1355
[7] PHOTOSENSITIZED OXYGENATION OF A 7,8-DIHYDRO-8-OXOGUANOSINE DERIVATIVE - FORMATION OF DIOXETANE AND HYDROPEROXIDE INTERMEDIATES (VOL 117, PG 474, 1995)
SHEU, C
FOOTE, CS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) : 4726 - 4726
[8] SYNTHESIS OF 2'-DEOXY-7,8-DIHYDRO-8-OXOGUANOSINE AND 2'-DEOXY-7,8-DIHYDRO-8-OXOADENOSINE AND THEIR INCORPORATION INTO OLIGOMERIC DNA
BODEPUDI, V
SHIBUTANI, S
JOHNSON, F
CHEMICAL RESEARCH IN TOXICOLOGY, 1992, 5 (05) : 608 - 617
[9] METHYLENE BLUE-MEDIATED PHOTOOXIDATION OF 7,8-DIHYDRO-8-OXO-2'-DEOXYGUANOSINE
BUCHKO, GW
WAGNER, JR
CADET, J
RAOUL, S
WEINFELD, M
BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1995, 1263 (01): : 17 - 24
[10] Comparative studies between 8-oxo-7,8-dihydro-2′-deoxyguanosine and 8-methoxy-2′-deoxyguanosine oxidation by singlet oxygen
Martinez, GR
Gasparutto, D
Medeiros, MHG
Ravanar, JL
Cader, J
Di Mascio, P
FREE RADICAL BIOLOGY AND MEDICINE, 2003, 35 : S106 - S107

← 1 2 3 →