Abstract
The condensation products of aldoses with aminoguanidine exist in aqueous solution at pH 6 as cyclic pyranosylaminoguanidines with the protonated aminoguanidine substituent at C-1 equatorial, and at pH 12 and in methyl sulfoxide as acyclic E-carboximidamidehydrazones. The cyclic isomers are present exclusively when mineral acid salts of the condensation products are dissolved in methyl sulfoxide. The sites of protonation and tautomerism at the aminoguanidine moiety have been studied by 1H-, 13C-, and 15N-n.m.r. methods, and mechanisms for the pH-dependent cyclic-acyclic interconversion are discussed.
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