Studies of 2-amino-2-deoxy- dl-glyceraldehyde. Identification of an n-acetyl derivative amongst the degradation products of the ovalbumin glycopeptide

Abstract

Reduction of ethyl 2-amino-3,3-diethoxypropionate with lithium aluminium hydride yields the acetal, CH 2OH·CHNH 2·CH(OC 2H 5) 2 ( 1). The product obtained on hydrolysis of 1 with concentrated hydrochloric acid is stable only in acid solution and behaves as a hydrate or a polymer of CH 2OH·CH N + H 3·CHO Cl −. It affords a crystalline semicarbazone hydrochloride ( 2), 2,4-dinitrophenylhydrazonehydrochloride ( 3), and dithioacetal oxalate ( 4). Other acyl and alkyl derivatives have been prepared directly from compound 1. The aldehyde, CH 2OH.CH(NHCOCH 3).CHO, which has only been identified in solution, should be formed after the Smith degradation of certain polysaccharides that contain amino sugars. The diethyl acetal 12 and its O-methyl derivative 15, the 2,4-dinitrophenylhydrazone 13, and the ethylene dithioacetal 14 of this aldehyde have been prepared. The derivative 14 was also isolated from the Smith-degradation products of the ovalbumin glycopeptide after mercaptolysis.