New synthesis of rethrolones

Buechi, George; Minster, David K.; Young, J. C. F.

doi:10.1021/ja00746a053

Cited by 22 publications

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“…The intermediacy of ii in the production of dinucleotide 1 from the alkali-labile lesion i (Schemes I, IV, and VI) is well precedented chemically (Büchi et al, 1971;Stork et al, 1975;Floyd, 1978) and provides support for the overall mechanistic scheme presented. The use of an alkylamine to control the mode of collapse of ii (iii) as shown in Scheme IV is novel and suggests some interesting opportunities for the manipulation of nucleic acid structure.…”

Section: Discussionmentioning

confidence: 55%

Chemistry of the alkali-labile lesion formed from iron(II) bleomycin and d(CGCTTTAAAGCG)

Sugiyama

Murugesan

et al. 1988

Biochemistry

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Two sets of products are formed from DNA upon treatment with Fe(II).bleomycin + O2. One set, which is believed to derive from a C-4' hydroperoxy derivative of the DNA deoxyribose moiety, includes the four possible base propenals, as well as DNA oligomers having deoxynucleoside 3'-(phosphoro-2"-O-glycolates) at their 3'-termini. The other set of products consists of free bases and alkali-labile lesions, the latter of which had not previously been characterized structurally. By use of the self-complementary dodecanucleotide d(CGCTTTAAAGCG) having a site modified by Fe-bleomycin three nucleotides from the 5'-end, it has been possible to characterize the alkali-labile product as a C-4' hydroxyapurinic acid. When the bleomycin-treated dodecanucleotide was treated with agents that effected decomposition of the alkali-labile lesion, products of the form CpGpx were obtained, and these proved useful for structural characterization of the alkali-labile lesion. Treatment with alkali produced CpGpx, where x was 2,4-dihydroxycyclopentenone. Alternatively, treatment with hydrazine provided a pyridazine derivative, and aqueous alkylamines led to formation of CpGp itself. The structures of all dinucleotides produced from the alkali-labile lesion were verified by direct comparison with authentic synthetic samples.

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Section: Discussionmentioning

confidence: 55%

Chemistry of the alkali-labile lesion formed from iron(II) bleomycin and d(CGCTTTAAAGCG)

Sugiyama

Murugesan

et al. 1988

Biochemistry

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ChemInform Abstract: NEUARTIGE SYNTH. VON RETHROLONEN

Buechi¹,

Minster²,

Young³

1971

Chemischer Informationsdienst. Organische Chemie

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Chemistry and biosynthesis of natural pyrethrins

Crombie

1980

Pestic. Sci.

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A short account is given of the occurrence, separation, and properties of the insecticidal ester pyrethrins from Chrysantlmnum cineuariaefolium. Methods for the synthesis of the two component acids, chrysanthemic and 'chrysanthemumdicarboxylic acid' [3-(2-carboxyprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid], and the alcohols (rethrolones) are surveyed, and brief consideration is given to the limited knowledge of the biosynthesis of this group of compounds. Osmium

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New synthesis of rethrolones

Cited by 22 publications

References 1 publication

Chemistry of the alkali-labile lesion formed from iron(II) bleomycin and d(CGCTTTAAAGCG)

Chemistry of the alkali-labile lesion formed from iron(II) bleomycin and d(CGCTTTAAAGCG)

ChemInform Abstract: NEUARTIGE SYNTH. VON RETHROLONEN

Chemistry and biosynthesis of natural pyrethrins

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