Lactosylamine, derivs

In alcoholic solution, lactose reacts with ammonia, aniline, do-decylamine, urea, guanidine, and hydroxylamine, respectively, to give lactosylamine derivatives. W-Octadecyllactosylamine was formed by condensing octadecylamine with lactose in 2-propanol-water (5 3 vol./ vol.) at room temperature. Occasionally, presence of a trace of acidic catalyst, such as ammonium chloride, zinc chloride, or hydrogen chloride may be necessary, especially if the amine is a weak base. p-Amino-phenol and p-phenetidine condense with lactose under such conditions. Condensation of lactose with o-phenylenediamine gives a quinoxaline (41), which is transformed into a flavazole derivative (42) on reaction with phenylhydrazine. The existence of a molecular compound of lactose with... 

Interest in iV-lactosylamine derivatives of various sulfa drugs has arisen from their ease of dissolution in water such compounds include derivatives of sulfanilamide, sulfapyridine, and sulfaguanidine. ... 

Several JV-nitroso derivatives of amino-sugars have been reported. For example, the L-enantiomers of streptozoticin and chlorozoticin, (28) and (29) respectively, have been prepared. The ureido-substituent group which is responsible for the anti-tumour activity of chlorozoticin (29), has been attached to the amino-groups of maltosylamine, cellobiosylamine, and lactosylamine and the products possessed marked anti-tumour activity.Additionally, A-nitroso derivatives of aldose-amino-acid adducts formed by the Maillard reaction, have been synthesized, and are believed to be present in foodstuffs which contain nitrite as... 

Glycosylurea and thiourea derivatives, e.g. (19), were synthesized by condensation of alkyl isocyanates and isothiocyanates respectively, with jS-D-glucopyranosylamine and fi-lactosylamine, as non-ionic detergents of particular interest for extraction of membrane proteins. Various l-( -D-glycosyl)-derivatives of diphenylhydantoin and hydrochlorothiazide were synthesized in an attempt to enhance the hydrophilicity and biological activity of these materials. Conformation analysis and X-ray structures of some 1,2- and 1,3-fused glycosylamine derivatives are included in Chapters 21 and 22. 

Pestman et al. [64] synthesized eight homologous series V-acetyl- and N-propionyl-A-alkylglucosyl/lactosylamines XXIII R a/XXVn R a,b and N-acetyl- and A-propionyl-A-alkyl-1-amino-1-deoxyglucitols/lactitols XXIV/ XXVIII R a,b (Fig. 8) with high yields of the final acyl derivatives. They determined the CMC values and the thermodynamic parameters of micel-lization by titration microcalorimetry. The results can be summarized as follows ... 

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