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- W2057384805 abstract "Abstract Three diazirines 2-azi-2-deoxy- d - arabino -hexitol (4) , its 1-deoxy analogue (5) , and 3-azi-3,6-dideoxy- l - xylo -hexitol (9) were synthesised and their products of photolysis analysed by TLC. Diazirine 4 gave exclusively 2-deoxy- d - arabino -hexose (12), 5 gave predominantly 1,2-dideoxy- d - erythro -3-hexulose (10) and 1-deoxy- d -glucitol (11) , and 9 did not yield any main product. Carrying out the irradiation of 4 in D 2 O gave selectively (2 S )-2-deoxy- d - arabino -(2- 2 H)hexose (12a) . The results indicate that photolysis of a diazirine flanked by a hydroxymethyl group, as in compound 4 , leads to a rapid and stereoselective intramolecular reaction of the intermediate. This may be an explanation of why compound 4 is ineffective as a photoaffinity reagent for mannitol permease ( d -mannitol-specific enzyme II) of the E. coli phosphotransferase system for which it is a substrate. A secondary hydroxymethylene group has a less pronounced effect and still allows some reaction with the medium." @default.
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- W2057384805 date "1993-02-01" @default.
- W2057384805 modified "2023-10-16" @default.
- W2057384805 title "Photolysis of 2-azi-2-deoxy-d-arabino-hexitol and analogous hexitols; the ineffectiveness of certain carbohydrate diazirines as photoaffinity labels" @default.
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- W2057384805 doi "https://doi.org/10.1016/0008-6215(93)84209-o" @default.
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