Ureides, glycosyl

A novel class of inhibitors, glycosyl ureides, were identified Srivastava et al. to compete with the NAD+. Five compounds with (81)... 

In summary, the strength of wood panels tested here did not hold up when the urea/carbohydrate molar ratio was lowered to 0.125 1, but did not suffer drastically when the caustic components of the adhesive were reduced by a third. Glycosyl ureides were the only intermediates identified in the sequence of reactions leading from monosaccharide to polymer, because of the quickly-escalating multiplicity of products. 

From their discovery, the glycosyl ureides have been of interest from a biochemical standpoint. The fact that D-glucose and urea occur in human blood in approximately equimolar concentrations (about 0.006 M) has led to speculation and to some investigation of the metabolic role of these compounds. Mayer, in a series of metabolic experiments with dogs, attempted to determine whether 1-D-glucosylurea is a natural constituent of normal or of pathological blood or urine. 

Aside from their biochemical implications, the glycosyl ureides have found application in the paper, textile, - and food industries. 

The cyclitol derivatives of streptomycin (streptidine and strepturea), although not strictly glycosyl ureides, are mentioned here since they are close relatives of the series. ... 

K. Quehl, U. 8. Pat. 2,116,640 (1938) Chem. Abstracts, 38, 500 (1938). Although this reference has been cited in relation to the glycosyl ureides [W. W. Pigman, The Carbohydrates, Academic Press Inc., N. Y., 1967, p. 415], the products described are merely physical mixtures of urea and n-glucoce in the form of molecular compounds. ... 

Requirements of simplicity and uniformity in nomenclature suggest that the Rules of the International Union of Pure and Applied Chemistry with regard to simple urea derivatives and to carbohydrates be applied to the glycosyl ureides. Thus, in this review the A-glycosides of urea, thiourea, and guanidine are included, with generic classifications as follows. 

This compound is almost certainly a/J-n-glucopyranosyl derivative however, since (for most members of these series) neither the ring structure (furanose or pyra-nose) nor the configuration at the anomeric carbon atom has been definitely established, these characteristics are not specified in the Tables of glycosyl ureides in the present Chapter. 

Johnson and Bergmann, as well as Helferich and Kosche, noted the possibility that the glycosyl ureides might be utilized as intermediates for an improved method of synthesis of pyrimidine nucleosides. Fischer s method was used for obtaining 1-n-glucosylurea as well as 1-n-arabinosyl-urea and 1,3-di-n-xylosylurea. 

As a representative member of the glycosyl ureides, the physical properties of 1-D-glucosylurea are listed here in detail. 

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