Pyrimidine Dimers: UV‐Induced DNA Damage

Iwai, Shigenori

doi:10.1002/9783527623112.ch5

Cited by 9 publications

(11 citation statements)

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“…Apart from the reviews already cited, very useful information about synthetically relevant [2 + 2] photocycloaddition chemistry can be found in reviews devoted to the application of photochemical reactions to natural product synthesis. 65 − 67 Limited attention has been given in the present review to [2 + 2] photocycloaddition reactions, which occur in the solid state (mostly as [2 + 2] photodimerization), 68 − 70 in biological systems, 71 , 72 or in confined media. 73 − 75 The [2 + 2] photocycloaddition to arenes, the ortho -photocycloaddition, 76 − 79 is not covered in this review, either.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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“…The major products of these reactions are cyclobutane pyrimidine dimers (CPDs) and pyrimidine(6–4)pyrimidone photoproducts ((6–4) photoproducts 1 ) (1). The simplest repair pathway for these UV lesions involves photoreactivation of the UV-damaged DNA, which uses the blue to near-UV light (300–500 nm) in sunlight to maintain genetic integrity (2,3).…”

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confidence: 99%

Role of the Carbonyl Group of the (6−4) Photoproduct in the (6−4) Photolyase Reaction

et al. 2009

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The (6–4) photoproduct, which is one of the major UV-induced DNA lesions, causes carcinogenesis with high frequency. The (6–4) photolyase is a flavoprotein that can restore this lesion to the original bases, but its repair mechanism has not been elucidated. In this study, we focused on the interaction between the enzyme and the 3’ pyrimidone component of the (6–4) photoproduct, and prepared a substrate analog in which the carbonyl group, a hydrogen-bond acceptor, was replaced with an imine, a hydrogen-bond donor, to investigate the involvement of this carbonyl group in the (6–4) photolyase reaction. UV irradiation of oligodeoxyribonucleotides containing a single thymine–5-methylisocytosine site yielded products with absorption bands at wavelengths longer than 300 nm, similar to those obtained from the conversion of the TT site to the (6–4) photoproduct. The nuclease digestion, MALDI-TOF mass spectrometry, and the instability of the products indicated the formation of the 2-iminopyrimidine-type photoproduct. Analyses of the reaction and the binding of the (6–4) photolyase using these oligonucleotides revealed that this imine analog of the (6–4) photoproduct was not repaired by the (6–4) photolyase, although the enzyme bound to the oligonucleotide with considerable affinity. These results indicate that the carbonyl group of the 3’ pyrimidone ring plays an important role in the (6–4) photolyase reaction. Based on these results, we discuss the repair mechanism.

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“…These UV lesions inhibit DNA replication and transcription, thus leading to cell death or mutagenesis and carcinogenesis, if they are not repaired correctly . To maintain their genetic integrity, organisms have developed various DNA repair systems.…”

Section: Introductionmentioning

confidence: 99%

Repair of (6‐4) Lesions in DNA by (6‐4) Photolyase: 20 Years of Quest for the Photoreaction Mechanism

Yamamoto

Plaza

Brettel

2017

Photochem & Photobiology

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Exposure of DNA to ultraviolet (UV) light from the Sun or from other sources causes the formation of harmful and carcinogenic crosslinks between adjacent pyrimidine nucleobases, namely cyclobutane pyrimidine dimers and pyrimidine(6-4)pyrimidone photoproducts. Nature has developed unique flavoenzymes, called DNA photolyases, that utilize blue light, that is photons of lower energy than those of the damaging light, to repair these lesions. In this review, we focus on the chemically challenging repair of the (6-4) photoproducts by (6-4) photolyase and describe the major events along the quest for the reaction mechanisms, over the 20 years since the discovery of (6-4) photolyase.

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Pyrimidine Dimers: UV‐Induced DNA Damage

Cited by 9 publications

References 246 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Role of the Carbonyl Group of the (6−4) Photoproduct in the (6−4) Photolyase Reaction

Repair of (6‐4) Lesions in DNA by (6‐4) Photolyase: 20 Years of Quest for the Photoreaction Mechanism

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Pyrimidine Dimers: UV‐Induced DNA Damage

Cited by 9 publications

References 246 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Role of the Carbonyl Group of the (6−4) Photoproduct in the (6−4) Photolyase Reaction

Repair of (6‐4) Lesions in DNA by (6‐4) Photolyase: 20 Years of Quest for the Photoreaction Mechanism

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions