J. Scott
Sep 1, 1970
Citations
0
Influential Citations
16
Citations
Journal
Carbohydrate Research
Abstract
Abstract The reaction of 2-amino-2-deoxyaldoses with isothiocyanates goes through three stages, producing a thiourea ( 1 ), which cyclises to a 5-hydroxyimidazolidine-2-thione ( 4 ) with concomitant opening of the sugar ring. A molecule of water can then be lost, with the formation of a furano ring, the imidazolidine-2-thione remaining intact in a fused, bicyclic structure ( 3 ). Products ( 3 ) derived from 1-amino-1-deoxy-2-ketoses are spiro compounds. Compound 4 is stable in neutral or alkaline solution, but converts quickly into 3 in acid. The conversion into 4 is extremely rapid, and its existence is inferential. Conversion of 4 , with loss of 1 mole of water per mole, into either an imidazole-2-thione ( 6 ) or a C-5 substituted imidazolidine-2-thione ( 3 ) is discussed, utilising the pseudo-basic properties of 4 . Mixtures of products 4 and 3 are separable by electrophoresis in tungstate and borate buffers. Electrophoretic mobilities of a number of amino-sugar derivatives are given.