Evidence that the (6-4) photolyase mechanism can proceed through an oxetane intermediate

被引:18
作者
Asgatay, Saadia [1 ]
Petermann, Christian [1 ]
Harakat, Dominique [2 ]
Guillaume, Dominique [1 ]
Taylor, John-Stephen [3 ]
Clivio, Pascale [1 ]
机构
[1] Univ Reims, Inst Chim Mol Reims, UFR Pharm, CNRS,UMR 6229, F-51096 Reims, France
[2] UFR Sci Exactes & Nat, F-51687 Reims 2, France
[3] Washington Univ, Dept Chem, St Louis, MO 63130 USA
关键词
D O I
10.1021/ja805214s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Using the analogue of TpT methylated at the 3'-end N(3) position (Tpm(3)T), we demonstrate that when the oxetane/(6-4) pathway is precluded, water addition occurs at the 3'-end C6 position of the oxetane intermediate to provide its opening. Photoreversal of this (6-4) photoproduct C6 hydrate brings the first experimental evidence that the (6-4) photolyase repair can proceed through an oxetane intermediate.
引用
收藏
页码:12618 / +
页数:3
相关论文
共 29 条
[1]   Electrochemical approach to the repair of oxetanes mimicking DNA (6-4) photoproducts [J].
Boussicault, Fabien ;
Robert, Marc .
JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (43) :21987-21993
[2]  
Breitmaier E., 1987, Carbon-13 NMR spectroscopy
[3]   UVB and UVA radiation-mediated damage to isolated and cellular DNA [J].
Cadet, J ;
Courdavault, S ;
Ravanat, JL ;
Douki, T .
PURE AND APPLIED CHEMISTRY, 2005, 77 (06) :947-961
[4]  
Cichon MK, 2002, ANGEW CHEM INT EDIT, V41, P767, DOI 10.1002/1521-3773(20020301)41:5<767::AID-ANIE767>3.0.CO
[5]  
2-B
[6]   NOVEL INSIGHT INTO THE STEREOCHEMICAL PATHWAY LEADING TO (6-4) PYRIMIDINE-PYRIMIDONE PHOTOPRODUCTS IN DNA [J].
CLIVIO, P ;
FOURREY, JL ;
GASCHE, J ;
FAVRE, A .
TETRAHEDRON LETTERS, 1992, 33 (12) :1615-1618
[7]   PHOTOCHEMISTRY OF DI(DEOXYRIBONUCLEOSIDE) METHYLPHOSPHONATES CONTAINING N-3-METHYL-4-THIOTHYMINE [J].
CLIVIO, P ;
FOURREY, JL ;
SZABO, T ;
STAWINSKI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7273-7283
[8]   DNA PHOTODAMAGE MECHANISTIC STUDIES - CHARACTERIZATION OF A THIETANE INTERMEDIATE IN A MODEL REACTION RELEVANT TO 6-4 LESIONS [J].
CLIVIO, P ;
FOURREY, JL ;
GASCHE, J ;
FAVRE, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5481-5483
[9]   Role of two histidines in the (6-4) photolyase reaction [J].
Hitomi, K ;
Nakamura, H ;
Kim, ST ;
Mizukoshi, T ;
Ishikawa, T ;
Iwai, S ;
Todo, T .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (13) :10103-10109
[10]   Model studies of the (6-4) photoproduct photolyase enzyme: Laser flash photolysis experiments confirm radical ion intermediates in the sensitized repair of thymine oxetane adducts [J].
Joseph, A ;
Prakash, G ;
Falvey, DE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (45) :11219-11225