C1′ Acylated Derivatives of 2′-Deoxyuridine. Photolabile Precursors of 2′-Deoxyuridin-1′-yl

Greenberg, Marc M.; Yoo, Dong Jin; Goodman, Brian K.

doi:10.1080/07328319708002519

Cited by 20 publications

(7 citation statements)

References 9 publications

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“…1 H NMR (DMSO-d6) (Figure S3): δ 9.39 (s, 1H, H-triazolyl), 8.45 (s, 1H, H-triazolyl), 8.43 (s, 1H, H-6), 7.29 (m, 5H, Ar-H of PhS), 6.08 (t, JH1′-H2′ ) 7.7 Hz, JH1′-H2′′ ) 6.2 Hz, 1H, H-1′), 5.27 (t, JOH-H5′ ) 5.1 Hz, JOH-H5′′ ) 4.6 Hz, 1H, 5′-OH), 5. 20…”

Section: Methodsmentioning

confidence: 99%

“…To address the mechanism of ROS-induced nucleic acid damage, Greenberg, − Giese, − and Cadet et al , reported the synthesis and characterization of a number of photolabile precursors of radical intermediates involved in radiation-induced nucleic acid damage. One of the precursors, 5-(phenylthiomethyl)-2‘-deoxyuridine, which yields a 5-methyl radical of thymine upon 254-nm irradiation, can give rise to a known cross-link lesion where the 5-methyl carbon atom of thymine and the C8 carbon atom of an adjacent guanine or adenine are covalently bonded. , This and earlier work by Box et al demonstrated that the intrastrand cross-link lesion can initiate from a single radical event.…”

Section: Introductionmentioning

confidence: 99%

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Independent Generation of 5-(2‘-Deoxycytidinyl)methyl Radical and the Formation of a Novel Cross-Link Lesion between 5-Methylcytosine and Guanine

2003

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Reactive oxygen species (ROS) can damage DNA. Although a number of single nucleobase lesions induced by ROS have been structurally characterized, only a few intrastrand cross-link lesions have been identified and characterized, and all of them involve adjacent thymine and guanine or adenine. In mammalian cells, the cytosines at CpG sites are methylated. On the basis of the similar reactivity of 5-methylcytosine and thymine toward hydroxyl radical and the similar orientation of adjacent thymine guanine (TG) and 5-methylcytosine guanine (mCG) in B-DNA, we predict that the cross-link lesion, which was identified in TG and has a covalent bond formed between the 5-methyl carbon atom of T and the C8 carbon atom of G, should also form at mCG site. Here, we report for the first time the independent generation of 5-(2'-deoxycytidinyl)methyl radical, and our results demonstrate that this radical can give rise to the predicted novel intrastrand cross-link lesion in dinucleoside monophosphates d(mCG) and d(GmC). Furthermore, we show that the cross-link lesion can also form in d(mCG) from gamma irradiation under anaerobic conditions.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Independent Generation of 5-(2‘-Deoxycytidinyl)methyl Radical and the Formation of a Novel Cross-Link Lesion between 5-Methylcytosine and Guanine

2003

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“…Chatgilialoglu et al reported that the 2‘-deoxyuridin-1-yl radical derived from 1‘- C -( tert -butyl)carbonyl-2‘- deoxyuridine as being pyramidal based on EPR spectroscopy . Also reported was the observation that both β- and α- anomers of this radical precursor gave an identical β/α-ratio (65/35) of 2‘-deoxyuridine upon irradiation in the presence of various thiols as hydrogen donors .…”

Section: Introductionmentioning

confidence: 99%

Nucleophilic Addition of Benzenethiol to 1‘,2‘-Unsaturated Nucleosides: 1‘-C-Phenylthio-2‘-deoxynucleosides as Anomeric Radical Precursors

et al. 2002

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The addition reaction of benzenethiol to the glycal portion of 1',2'-unsaturated uridine proceeds efficiently in the presence of Et(3)N. The mechanism involves nucleophilic attack of thiolate at the anomeric position in the rate-determining step, wherein conjugation between the nucleobase and the glycal portion is crucial. The derivative having a methyl group either at the 2'- or 6-position did not undergo this addition reaction, due to their sterically prohibited coplanarity. The 1',2'-unsaturated derivatives of thymine and adenine can also be used as substrates for this addition reaction. It was also shown that the resulting 1'-C-phenylthio-2'-deoxynucleosides serve as precursors for radical-mediated C-C bond formation at the anomeric position.

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“…(1)] through a number of currently disputed pathways. 1,2,5 We report herein an ex novo synthesis of tert-butyl ketone 6 9 and the mechanism of the formation of 2 [eqn. (1)].…”

mentioning

confidence: 99%

“…The recently reported synthesis of 6 has two major drawbacks: 9 (i) a known psiconucleoside triol, prepared by a low yielding, laborious procedure, is used as the precursor, 10 and (ii) a total lack of regioselectivity in the protection step of this triol is observed. For these reasons, we used as our precursor compound 3, readily available in diastereomerically pure form from the corresponding protected 1A,2A-didehydro-2A-deoxyuridine by a literature procedure.…”

mentioning

confidence: 99%

Fate of the C-1′ peroxyl radical in the 2′-deoxyuridine system

Chatgilialoglu¹,

Gimisis²

1998

Chem. Commun.

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C1′ Acylated Derivatives of 2′-Deoxyuridine. Photolabile Precursors of 2′-Deoxyuridin-1′-yl

Cited by 20 publications

References 9 publications

Independent Generation of 5-(2‘-Deoxycytidinyl)methyl Radical and the Formation of a Novel Cross-Link Lesion between 5-Methylcytosine and Guanine

Independent Generation of 5-(2‘-Deoxycytidinyl)methyl Radical and the Formation of a Novel Cross-Link Lesion between 5-Methylcytosine and Guanine

Nucleophilic Addition of Benzenethiol to 1‘,2‘-Unsaturated Nucleosides: 1‘-C-Phenylthio-2‘-deoxynucleosides as Anomeric Radical Precursors

Fate of the C-1′ peroxyl radical in the 2′-deoxyuridine system

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