Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Reduction of Aliphatic α-Hydroxycarbonyl Compounds
Part I. Reduction of Streptomycin at Controlled-potential Cathode
Kei-ichi TSUJI
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1961 Volume 25 Issue 6 Pages 432-440

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Abstract
The reduction of streptomycin with aluminum amalgam to dihydrodesoxystreptomycin (α-hydroxyaldehyde to monohydric alcohol, in its streptose moiety) is reproduced at dropping mercury electrode and at controlled-potential mercury pool electrode. The accompanying formation of dihydrostreptomycin, of which α-hydroxyl group is intact, depends upon the cathode potential and pH. Electrolysis at a potential corresponding to the relatively negative part of polarographic reduction wave and at relatively higher pH favors the formation of dihydro derivative and vice versa. This explains, from polarographic standpoint, the characteristic mode of reduction with aluminum amalgam. Electroreduction of streptomycin is applicable for the preparation of dihydrodesoxyderivative but not so for that of dihydro derivative.
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