N-Carbamoyl-D-glucosamine

The structure of a new antibiotic, CV-1 was determined to be 1,2-diamino-1,2-N,N'-carbonyl-1,2-dideoxy-alpha-D-glucose hydrate by spectral and chemical studies. CV-1 possessed a unique open ring hemiaminal structure. CV-1 synthesized from N-carbamoyl-D-glucosamine was identical to material isolated from fermentation.

N-carbamoyl-beta-D-glucopyranosylamine (NCG) is a compound, which can chemically be synthesized by the condensation of glucose and urea by heating under acidic condition. In this study, we isolated and identified NCG and its anomer from human serum. This is the first study showing the occurrence and isolation of NCG from a natural source. The NCG level in human serum was estimated to be 71+/-33 microM using a glucose-3-dehydrogenase-based assay. Because NCG is not commercially used in foods or drugs, we conclude that the NCG isolated from human serum is synthesized from blood glucose and urea in vivo.

A statistical investigation was carried out on the distribution of serum N-carbamoyl-beta-D-glucopyranosylamine (NCG) among various patient groups. The serum NCG levels of patients treated in the departments of hemodialysis (131 +/- microM), nephritic syndrome (47 +/- 54 microM), and diabetes mellitus (55 +/- 70 microM) were significantly higher (p < 0.01) than those in other internal disease patients (18 +/- 22 microM) and healthy volunteers (6 +/- 22 microM). The serum NCG level was greatly reduced by hemodialysis therapy, however a return to initial NCG levels was observed within about one week. These results indicate that a high serum NCG level is a feature of renal failure patients, and a relationship was demonstrated between hyperuremia and NCG formation and accumulation in blood.