Messrs Morrell and Bellars, Compounds of Guanidine, etc. 79 



Same Compounds of Guanidine with Sugars. By R. S. Morrell, 

 M.A., Gonville and Caius College, and A. E. Bellars, B.A., 

 Magdalene College. 



[Bead 27 February 1905.] 



The action of alkalies and especially of ammonia on sugars has 

 been the subject of a number of papers by Lobry de Brliyn and 

 his colleagues van Leent and van Ekenstein 1 . They have described 

 crystalline compounds of ammonia with glucose, galactose, rham- 

 nose, arabinose, and xylose, of the nature of osamines, but they 

 consider that maltose and lactose form additive products with 

 ammonia. Several of these osamines crystallise with molecules 

 of alcohol of crystallisation. The compound of ammonia with 

 fructose, fructosamine, C 6 H 9 4 N, is of interest in its connection 

 with chitosamine, CHOCHNH 2 (CHOH) 3 CH 2 OH, from which it 

 may be prepared. Fructosamine is by far the most stable of the 

 osamines which generally evolve ammonia at their melting points, 

 and even there is a loss of ammonia when aqueous solutions of 

 osamines are heated to boiling. The study of the influence of 

 dilute alkalies on the optical activity of solutions of glucose led 

 Lobry de Briiyn and van Ekenstein to the conclusion that glucose, 

 fructose, and mannose are reciprocally transformable into one 

 another in aqueous solution. 



Several years ago it was noticed by one of us that an alcoholic 

 solution of guanidine gave white minutely crystalline precipitates 

 with alcoholic solutions of glucose and rhamnose. The com- 

 pounds obtained were exceedingly hygroscopic and could not be 

 recrystallised from any solvent; moreover they were never free 

 from inorganic material, since the guanidine was prepared from its 

 hydrochloride by the action of sodium ethylate. If guanidine 

 were prepared from the carbonate by decomposing the salt with 

 less than the calculated quantity of baryta, and the concentrated 

 aqueous solution were freed from excess of guanidine carbonate by 

 addition of absolute alcohol, it was found that compounds of the 

 base with sugars was obtained free from ash. From ethylic alcohol 

 solutions glucose, fructose, galactose, rhamnose, and maltose were 

 precipitated combined with guanidine as microscopically crystalline 



1 Rec. des Trav. Chim. des Patj Bas, 12, 286 ; 13, 218 ; 14, 98, and 134 ; 16, 183 ; 

 18, 81. 



