Gulose 3- amino-3-deoxy

A. C. Richardson and H. O. L. Fischer, Cyclization of dialdehydes with nitromethane, Part VI. Preparation of 3- amino-1,6-anhydro-3-deoxy-p-D-gulose, -P-D-altrose and -p-D-idose derivatives and their characterization by means of inversion of mesyloxy groups,./. Am. Chem. Soc., 83 (1961) 1132-1139. 

W. Homer, L. Hough, and A. C. Richardson, Derivatives of 2-amino-2-deoxy-D-gulose Synthetic and conformational studies,/. Chem. Soc., Sect. C (1971) 99-102. 

Similarly, 2-amino-2-deoxy-D-galactose was converted into 2-amino-2-deoxy-D-gulose by solvolysis of methyl 2-acetamido-2-deoxy-3-0-mesyl-a-D-galactopyranoside.82... 

Deoxy-2-(2-hydroxy-I- naphthylmethyl- ene)amino-D- gulose 186-188 [a]646i 150 2-methoxy- ethanol 178, 188... 

The structure of YA-56 was studied by Ohashi et al.36l. They showed that structural differences between PHM and YA-S6 existed in amine components I and III, and in the gulose moiety. They axe substituted by /3-hydroxy-L-valine, 4-amino-3,6-dihydroxy-2-methylhexanoic acid and 6-deoxy-L-gulose, respectively. The terminal amine was found to be 3-aminopropionamidine, which had not been found in natural PHMs. The total structure of YA-56X can be postulated as shown in Fig. 928.36) YA-56 Y has an additional component, 7-aminobutyric acid. But the position of this amino acid in the molecule is not yet known. 

When the pyrimidine nucleoside derivative (197) was treated with potassium cyanide in iV,W-dimethylformamide, there was evidence that the totally deblocked products contained the 3-amino-3-deoxy-D-galactose nucleoside (202), as well as the 4-amino-4-deoxy-D-gulose nucleoside (199). It was suggested that the aziridine (198), formed by nitrogen participation, was a precursor of (199), and that either the oxazoline (200), formed by oxygen participation, or the anhydronucleoside (201) intervened in the formation of (202). 

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