THE SYNTHESIS OF ANALOGS OF THE AMINONUCLEOSIDE FROM

Leon Goldman, Joseph W. Marsico, and Robert B. Angier ... Morris J. Robins, Robert W. Miles, Mirna C. Samano, and Roger L. Kaspar. The Journal of Orga...
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Aug. 20 1956

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captide containing the elements of sulfate and allyl drochloric acid a t room temperature was effective, isothiocyanate, and subsequently on the alkaline but we have mostly used a modification of Yamada's hydrolysis of sinigrin to @-D-l-thioglucopyranose.2 assayg for bound hydroxylamine, cleavage in However, I does not accord with the known 3 M sulfuric acid containing 2,4-dinitropheq-lfacts'~~ that , ~ sinigrin and analogs yield on direct hydrazine for 2 hours a t 95-100'. The hydroschemical degradation, not the amines (RNH2) ex- ylamine liberated was identified by paper chropected from I, but nitriles (RCN) and carboxylic matographylO 0.46-0.51 in 7 :3 methanolacids containing the same number of carbon atoms 6 N hydrochloric acid, detected by three specific as the enzymatically formed isothiocyanates (RN- reagents), determined quantitatively by the CsakyYamada methodg or as ferric benzhydroxamate,' l CS). SC~Hii06 R-[ -S=C