3-Amino sugars isolation

Mycosamine differs from most of the other amino sugars isolated from antibiotic substances in not being V-methylated.86 The tetraacetate XXVI of mycosamine (XXV) can be isolated by acetolysis of nystatin or of the antifungal antibiotic substance amphotericin B, and it yields the acetamido derivative XXVII on catalytic deacetylation. 

Derivation Amino sugar isolated from chondroitin sulfate. 

Amino-sugars and Related Compounds. Part IV. Isolation and Properties of Oligosaccharides Obtained by Controlled Fragmentation of Chitin, S. A. Barker, A. B. Foster, M. Stacey, and J. M. Webber, J. Chem. Soc., (1958) 2218 - 2227. 

Howell88 considered it to be a derivative of D-glucuronic acid, but this view was not confirmed by Charles and Scott,89 who isolated a crystalline barium heparinate from beef lung and detected the presence in it of an amino sugar. 

Reaction of nitromethane and monosaccharide-derived dialdehydes is a useful tool that has been broadly used for the preparation of nitro and amino sugars, and carbocycles.30 Dialdehydes can easily be obtained by oxidative cleavage of conveniently protected monosaccharides with sodium periodate. Their subsequent Henry reaction with a nitroalkene, commonly nitromethane, usually gives isomeric mixtures that require the isolation of the major isomer.31 Thus, treatment of the D-ribose derivative 27 with sodium periodate gave dialdehyde 28, which was subjected to a Henry reaction with nitromethane, to afford nitrosugar 29 as an epimeric mixture (Scheme 11).32... 

Debono, M. and Molloy, R.M., Isolation and structure of the novel branched-chain amino sugar derived from antibiotic A35512B, J. Org. Chem., 45, 4685, 1980. 

Spectinomycin Spectinomycin, 4a,7,9-trihydroxy-2-methyl-6,8-fcw-(methylamino)-per-hydroxypyrano-[2,3-b]benzodioxan-4-one (32.7.1), which is isolated from products of the actinomycete Streptomyces spectabilis, is an aminocyclitol, yet it is not an aminoglycoside antibiotic since it does not contain either an amino sugar region or a glycoside bond [316-324]. 

Uridine 5 -(2-acetamido-2-deoxy-a-n-gIucopyranosyluronic acid pyrophosphate) (36) was isolated from extracts of Achromobacter georgiopolitanum14Sa and Micrococcus lysodeikticus.149b The ester of uridine 5 -pyrophosphate with an unusual amino sugar, namely, a 2-acetamido-2,4,6-trideoxyhexose of unknown configuration, has... 

The protonated amino group, however, has no nucleophilic activity, and does not form a hemiacetal an amino sugar can, therefore, be obtained, as a salt, in an otherwise unfavorable form. For example, 6-amino-6-deoxy-L-sorbose can be isolated as the hydrochloride of a furanose form (22) (presumably a). In alkaline solution, immediate ring-expansion to the pyranose form (23) occurs127 this reaction can be reversed under strongly acidic conditions. 4-Amino-4,6-dideoxy-D-glucose hydrochloride forms a 35 65 mixture of the a- and / -pyranose forms in solution.128... 

D-Apiose can be isolated from parsley and is a component of the cell wall polysaccharide of various marine plants. Among its novel structural features is the presence of only a single chirality center. L-Vancosamine is but one portion of vancomycin, a powerful antibiotic that has emerged as one of only a few antibiotics that are effective against drug-resistant bacteria. L-Vancosamine is not only a branched-chain carbohydrate, it is a deoxy sugar and an amino sugar as well. 

---