Photochemische reaktionen von uracil und uridin

Wacker, A.; Weinblum, D.; Träger, Lothar; Moustafa, Zeinab H.

doi:10.1016/s0022-2836(61)80086-7

Cited by 53 publications

(7 citation statements)

References 11 publications

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“…Mixed cyclobutane dimers of thymine and uracil have been produced by uv irradiation of DNA,32-35 thymine-uracil mixtures, [36][37][38][39] and cytidine-and deoxycytidine-thymidine mixtures. 35 Although the mixed thymine-uracil dimers have been detected, no structure elucidation has been done.…”

Section: T H Imentioning

confidence: 99%

Synthetic spectroscopic models related to coenzymes and base pairs. IX. "Abbreviated" dinucleosides of thymidine and deoxyuridine and their photoproducts

Logue¹,

Leonard²

1972

J. Am. Chem. Soc.

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The photodimerization of two thymines and of thymine and uracil held in close proximity by a ribofuranose backbone has been examined. "Abbreviated" dinucleosides 5'-deoxy-5'-(l-thyminyl)thymidine (3a) and 2',5'-dideoxy-5'-(l-thyminyl)uridine (3b) have been synthesized via ring closure of the appropriate 5'-N-(3-mtthoxy-a-methylacryloyl)ureidodeoxynucleosides 2a and 2b. Intermediates 2a and 2b were prepared by the treatment

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Section: T H Imentioning

confidence: 99%

Synthetic spectroscopic models related to coenzymes and base pairs. IX. "Abbreviated" dinucleosides of thymidine and deoxyuridine and their photoproducts

Logue¹,

Leonard²

1972

J. Am. Chem. Soc.

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“…photodimerisation reactions of thymine or uracil derivatives) were conducted in order to understand the photodeactivation mechanism of DNA. 12, 13 In addition, studies of phototransformations occurring in ice under astrophysical conditions suggested a possible interstellar origin for some organic compounds found on Earth. [14][15][16] In the past decade, research results have provided a sufficient evidence that organic as well as inorganic compounds can undergo efficient solar light-induced chemical transformations in ice and snowpack.…”

Section: Introductionmentioning

confidence: 99%

Comparison of the effects of UV, H2O2/UV and γ-irradiation processes on frozen and liquid water solutions of monochlorophenols

Klánová

Klán

Heger

et al. 2003

Photochem Photobiol Sci

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The effects of UV irradiation, both in the presence and absence of hydrogen peroxide, as well as of gamma irradiation on 2- and 4-chlorophenol in a solid water ice matrix have been studied and compared to those effects known to occur in aqueous solutions. While UV photolysis (>280 nm) of monochlorophenols leads to efficient coupling reactions in ice and photosolvolysis products in liquid water; hydroxylation to chlorobenzenediols is the main pathway in the presence of H2O2 in both phases. The results show that the solute molecules accumulate in a layer surrounding the ice crystal walls during the freezing process, where they then react. The radiation chemistry of chlorophenol ice samples involves preferential coupling reactions at -78 degrees C rather than reactions with the OH radicals produced by cleavage of water molecules under the conditions employed (1 kGy h(-1)). The apparent similarities between the chemistry in the UV/H2O2-treated liquid and solid, and y-irradiated liquid and solid samples are discussed. It is suggested that the reactions of OH radicals within polycrystalline ice or snow are important natural processes that should be considered in environmental, ice-core or astrophysical research.

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“…Identification and determination of the relative yields of the dimers formed when uracil is irradiated in frozen solution In the early 1960s, a number of workers noted that irradiation of Ura in the frozen state at dry ice temperature yields product(s) that were shown to have the character of CBDs (40–43). However, there was not uniform agreement among these researchers concerning the number and properties of the dimers formed in this photochemical reaction.…”

mentioning

confidence: 99%

“…However, there was not uniform agreement among these researchers concerning the number and properties of the dimers formed in this photochemical reaction. For example, Wacker and coworkers (42) indicated that one isomer was formed, while Smith (43) found that two products appeared after paper chromatography, one with an R f of 0.12 and the other with an R f of 0.01. Smith noted that the faster moving material converted into the slower moving material upon standing, while the slower moving compound could be reconverted to the faster moving dimer by treatment with acid, alkali or heat.…”

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confidence: 99%

The Photochemistry of Uracil: A Reinvestigation

Shetlar¹,

Basus²

2010

Photochem & Photobiology

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Results from a re-examination of the photochemical reactions undergone by uracil (Ura) are presented. Irradiation of Ura in frozen aqueous solution at -78.5°C produces two diastereomeric (6-4) products, namely the cis and trans isomers of 5-hydroxy-6-4'-(pyrimidin-2'-one)-5,6-dihydrouracil. Upon heating in 0.1m HCl, each of these compounds decomposes to form 6-4'-(pyrimidin-2'-one)uracil. In addition, evidence for production of a hydrate of a trimer of Ura is presented, Irradiation of this compound at 254nm forms Ura and a (6-4) adduct as products. The compounds 5-4'-(pyrimidin-2'-one)uracil and 6-hydroxy-5,6-dihydrouracil were also present after Ura was irradiated in frozen aqueous solution. Cyclobutane dimers (CBDs) are formed when Ura is irradiated in the frozen aqueous state, in fluid aqueous and acetonitrile solution and in the presence of photosensitizers (e.g. acetone). Published information, concerning the identity and relative quantitative importance of the four CBD isomers (cis-syn, cis-anti, trans-syn and trans-anti) formed in these photochemical systems, is incomplete and often in substantial disagreement. Using chemical methods in conjunction with HPLC, the identity and relative amounts of the four dimers have been determined in each of these systems. Consequently, a number of inconsistencies found in the literature concerning dimer product identity and quantitative distribution have been resolved.

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Photochemische reaktionen von uracil und uridin

Cited by 53 publications

References 11 publications

Synthetic spectroscopic models related to coenzymes and base pairs. IX. "Abbreviated" dinucleosides of thymidine and deoxyuridine and their photoproducts

Synthetic spectroscopic models related to coenzymes and base pairs. IX. "Abbreviated" dinucleosides of thymidine and deoxyuridine and their photoproducts

Comparison of the effects of UV, H2O2/UV and γ-irradiation processes on frozen and liquid water solutions of monochlorophenols

The Photochemistry of Uracil: A Reinvestigation

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