Photochemical reactions of nucleic acid constituents. Peroxide-initiated reactions of purines with alcohols

Salomon, J.; Elad, D.

doi:10.1021/jo00959a044

Cited by 41 publications

(13 citation statements)

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“…crosslinking is less well understood than the role of pyrimidines. However, chemical studies have indicated that various alcohols and amines can form photo-adducts with purines (23,24). Since these groups are present in proteins, a role for purines in photoinduced crosslinking is at least a theoretical possibility (K.C.…”

Section: Discussionmentioning

confidence: 99%

Ultraviolet light-induced crosslinking of mRNA to proteins

Greenberg¹

1979

Nucl Acids Res

118

105

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Irradiation of intact or EDTA-dissociated L-cell polyribosomes with 254 nm UV light at doses of 1-2 x 10(5) ergs/mm2 extensively crosslinks mRNA to proteins. The crosslinked mRNA-protein complexes can be isolated on the basis of buoyant density in urea-containing CS2SO4 gradients that dissociate non-covalent complexes. Crosslinking of mRNA can also be assayed by phenolchloroform extraction. mRNA recovered from the crosslinked complexes by digestion with proteinase K has the same electrophoretic mobility in polyacrylamide gels as unirradiated mRNA. Therefore, irradiation does not either crosslink RNA molecules to RNA molecules or break phosphodiester bonds. With these methods it has been found that more than 70% of high molecular weight polydisperse mRNA, but only 25-40% of histone mRNA, can be crosslinked to protein. On the basis of buoyant density the histone mRNA-protein complex had a protein content of 26%, whereas the mean protein content of most non-histone mRNA-protein complexes was 65%. It is concluded that most mRNA in polyribosomes is in close contact with proteins, and that histone mRNA can be crosslinked to many fewer proteins that most other mRNAs.

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Section: Discussionmentioning

confidence: 99%

Ultraviolet light-induced crosslinking of mRNA to proteins

Greenberg¹

1979

Nucl Acids Res

118

105

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“…Results from the labor a-tory of Elad (Steinmaus et al, 1969(Steinmaus et al, , 1971Salomon and Elad, 1973) have shown the C-8 substitution of the adenine and guanine moieties can be induced to occur by both -y-ray irradiation and by the photolytic decomposition of DBP or dicumyl peroxide at wavelengths not absorbed by the purine bases. As discussed previously, the alkoxy radicals, generated through the decomposition of these free-radical initiators, react with the alcohol being studied to generate the corresponding a-hydroxyalkyl radicals.…”

Section: 32d Adenine Guanine and Related Compoundsmentioning

confidence: 99%

Cross-Linking of Proteins to Nucleic Acids by Ultraviolet Light

Shetlar

1980

Photochemical and Photobiological Reviews

100

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“…Previous literature reported the methodology to introduce hydroxyl functionality at the 8-position of a variety of purine derivatives using a peroxide-initiated photoreaction between the purine and alcohol. 27 This reaction served as a first step, placing the reactive hydroxyl group on caffeine allowing for further derivatization to a methacrylate. Scheme 1 depicts the photoreaction and conditions used to synthesize the methanol caffeine derivative.…”

Section: Resultsmentioning

confidence: 99%

“…This aromatic heterocycle, which contains hydrogen bond accepting carbonyls, noncovalently interacts with receptors and remains unaltered chemically . In the early 1970's, Salomon and coworkers reported the ability to incorporate hydroxyl functionality at the 8‐position of caffeine, adenine, adenosine, guanosine, and 2′‐deoxyguanosine. Figure depicts the chemical similarity between adenosine, caffeine, and the nucleobase adenine.…”

Section: Introductionmentioning

confidence: 99%

Free radical polymerization of caffeine‐containing methacrylate monomers

Nelson

Hemp

Chau

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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The incorporation of acrylic functionality into caffeine enables the preparation of a vast array of novel thermoplastics and thermosets. A two-step derivatization provided a novel caffeine-containing methacrylate monomer capable of free radical polymerization. Copolymers of 2-ethylhexyl methacrylate and caffeine methacrylate (CMA) allowed for a systematic study of the effect of covalently bound caffeine on polymer properties.1 H NMR and UV-vis spectroscopy confirmed caffeine incorporation at 5 and 13 mol %, and SEC revealed the formation of high molecular weight (co)polymers (>40,000 g/mol). CMA incorporation resulted in a multistep degradation profile with initial mass loss closely correlating to caffeine content. Differential scanning calorimetry, rheological, and thermomechanical analysis demonstrated that relatively low levels of CMA increased the glass transition temperature, resulting in higher moduli and elucidating the benefits of incorporating caffeine into polymers.

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Photochemical reactions of nucleic acid constituents. Peroxide-initiated reactions of purines with alcohols

Cited by 41 publications

References 1 publication

Ultraviolet light-induced crosslinking of mRNA to proteins

Ultraviolet light-induced crosslinking of mRNA to proteins

Cross-Linking of Proteins to Nucleic Acids by Ultraviolet Light

Free radical polymerization of caffeine‐containing methacrylate monomers

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