Ultraviolet and Γ‐ray‐induced Reactions of Nucleic Acid Constituents. Reactions of Purines With Amines

Salomon, J.; Elad, D.

doi:10.1111/j.1751-1097.1974.tb06469.x

Cited by 41 publications

(21 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Salomon and Elad (1974b) found that adenine formed 8-(a-aminoisopropyl)adenine while both adenine and adenosine formed a similar type of adduct with piperidine, in which the carbon alpha to the nitrogen of the piperidine ring was bound to the 8-carbon of the purine ring. Simil~r free"radical-initiated reactions ofthe purine bases in isopropanol were discussed in Section 3.3.2d; it was stated there that direct UV-induced reactions of adenosine with isopropanol lead to the same adducts as the free radical initiated reactions.…”

Section: 42b Adenine-and Adenosine-amine Systemsmentioning

confidence: 98%

“…A hydrogen alpha to the amino group of the alkyl amine was found to be required for reaction, as tbutylamine was unreactive. Elad and Salomon (1971) and Salomon and Elad (1974b) found that the photolysis of aqueous solutions of caffeine and isopropyl amine led to 8-isopropylcaffeine. They also isolated 8-a-aminoisopropylcaffeine from this reaction mixture.…”

Section: Adenine Guanine and Related Compoundsmentioning

confidence: 98%

“…Nor are there are any reports that indicate that directly photoexcited adenine, guanine, or closely related compounds are reactive toward the addition of side-chain analogs, such as amines. Elad and Salomon (1971), Salomon and Elad (1974b) and Stankunas et al (1971) studied the direct photochemical reaction of caffeine with amines. Stankunas et al (1971) found that the main products of photolysis of caffeine in aqueous solution with alkyl amines were the corresponding 8-alkyl caffeines.…”

Section: Adenine Guanine and Related Compoundsmentioning

confidence: 99%

See 2 more Smart Citations

Cross-Linking of Proteins to Nucleic Acids by Ultraviolet Light

Shetlar

1980

Photochemical and Photobiological Reviews

100

View full text Add to dashboard Cite

Section: 42b Adenine-and Adenosine-amine Systemsmentioning

confidence: 98%

Section: Adenine Guanine and Related Compoundsmentioning

confidence: 98%

Section: Adenine Guanine and Related Compoundsmentioning

confidence: 99%

See 1 more Smart Citation

Cross-Linking of Proteins to Nucleic Acids by Ultraviolet Light

Shetlar

1980

Photochemical and Photobiological Reviews

100

View full text Add to dashboard Cite

“…One possibility is that incorporation results from the alkylation of the 8 position of the dimethyladenine moiety in puromycin by suitable groups from the protein and/or nucleic acid portions of the ribosome (32,33). Regardless of the detailed mechanism, it is clear from ter to be true, the argument would have to be made that the reactive puromycin species generated photochemically has especially high reactivity toward L23, leading to the large amount of labeling observed.…”

Section: Discussionmentioning

confidence: 99%

Photoincorporation of puromycin and N-(ethyl-2-diazomalonyl)puromycin into Escherichia coli ribosomes.

Cooperman¹,

Jaynes²,

Brunswick³

et al. 1975

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

ABSTRACT[3HJPuromycin and N4ethyl-2-diazomalonylX3H]puromycin are incorporated into E. coli ribosomes on irradiation at 253.7 nm. Both compounds incorporate into both protein and nucleic acid. Two-dimensional gel electrophoresis of ribosomal protein shows that L23 is the major protein labeled by puromycin. Although incorporation is clearly a complex process, evidence is presented that L23 is labeled via an affinity labeling process, thus placing L23 at the aminoacyl-tRNA receptor (A) site. N.(ethyl-2-diazomalonyl)puromycin is a ribosomal ligand, as shown by its inhibition of two ribosomal assays, but it is not a good puromycin analog, and it is unclear whether its incorporation, which proceeds via both carbene-dependent and carbene-independent processes, results from affinity labeling.Affinity labeling (1) has found wide application as a tool for mapping complex biological structures, and has recently been applied to ribosomes (2-15, 40, 41). This technique uses either electrophilic or photolabile derivatives of biological ligands to form covalent bonds with the appropriate biological receptors. The advantages, at least in principle, of photolabile derivatives have been discussed elsewhere (16). As part of a large-scale effort to use photolabile antibiotic derivatives to map ribosome function, we have synthesized N-(ethyl-2-diazomalonyl)puromycin and studied its covalent incorporation into ribosomes on photolysis. During the course of this work we found that puromycin itself will photoincorporate into ribosomes. This paper reports the results of initial studies on these two incorporation processes. MATERIALS AND METHODSPuromycin dihydrochloride was obtained from Sigma.[3H]Puromycin, labeled in the methoxyl protons, was obtained from New England Nuclear. Ethyl-2-diazomalonyl chloride was prepared as described previously (17). Ribosomes used in all incorporation experiments were prepared from Escherichia coli Q13 bacteria harvested in late log phase by the method of Kurland (18). N-(ethyl-2-diazomalonyl)puromycin (N-EDMpuromycin) was N-EDMpuromycin was characterized by its ultraviolet spectrum, which is the sum of two isolated chromophores, puromycin and ethyl-2-diazomalonamide (Xma. 260 nm, Emax 23,000 M-1 cm'1). Brief photolysis of N-EDMpuromycin at 253.7 nm results in the appearance of an ultraviolet spectrum identical to that of puromycin. Further proof that the amino group is the site of derivatization rather than either of the two hydroxyl groups comes from the observations that N-EDMpuromycin is stable toward release of ethyl-2-diazomalonic acid on treatment with 0.1 N NaOH, and that on prolonged standing in alkaline aqueous or alcoholic solutions, N-EDMpuromycin isomerizes into a compound which is not readily photolyzed and whose ultraviolet spectrum indicates that it is a 1,2,3 triazole (Xm. 272, em. 28,000) (17).Although the triazole cannot be readily converted to an ethyl-2-diazomalonamide in water, the reconversion proceeds smoothly on dissolving the triazole in a 6% acetic acid/ chloroform solution....

show abstract

“…alcohols, amines and amino acids, suggest that in dilute aqueous solution photoalkylation occurs Linschitz and Conolly, 1968;Elad and Rosenthal, 1969;Evans and Wolfenden, 1970;Elad and Salomon, 1971;Stankunas et al, 1971;Salomon and Elad, 1974). Steinmaus et al (1969,1970) have presented chemical proof for the structure of the major photoproducts of adenine, adenosine, guanine and hypoxanthine, using isopropanol as the photoalkylating agent (Fig.…”

Section: Photoalkylationmentioning

confidence: 99%