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- W1259597789 abstract "This chapter describes the preparation of cryptofluorescent analogs of cobalamin coenzymes. Upper-axial (β-position) ligand analogs of methyl- and adenosylcobalamin are synthesized from cob(I)alamin and alkyl halides containing fluorescent R groups. Cob(I)alamin, which contains a cobalt atom in the + 1 oxidation state, is prepared by the reduction of cyanocobalamin with powdered zinc in aqueous ammonium chloride. Alkyl halide, derivatives of fluorescent adenosine analogs (1,N6-ethenoadenosine, formycin, 2,6-diaminonebularin and 2-aminonebularin), are conveniently prepared in high yield by direct halogenation at the 5’ position with thionyl chloride in the presence of hexamethylphosphoramide. The fluorescent R group dansyl (1-dimethylaminonaphthalene-5-sulfonyl) is coupled to cob(I)alamin after conversion to dansylamidopropyl chloride. A unique feature of these cobalamin analogs is that, although the halogenated precursors are highly fluorescent, the products emit no detectable fluorescence when excited at the absorbance maxima of their respective R groups. Quenching of the β-1igand R group fluorescence occurs probably as a result of intramolecular energy transfer between the ligand and the nonfluorescent corrinoid. Cleavage of the carbon-cobalt bond and release of the β ligand results in the reappearance of fluorescence. This cryptofluorescent property of cobalamin coenzyme analogs containing fluorescent R groups has been used to monitor their reactivity in model systems." @default.
- W1259597789 created "2016-06-24" @default.
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- W1259597789 date "1980-01-01" @default.
- W1259597789 modified "2023-09-25" @default.
- W1259597789 title "[3] Preparation of cryptofluorescent analogs of cobalamin coenzymes" @default.
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- W1259597789 doi "https://doi.org/10.1016/s0076-6879(80)67005-0" @default.
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