Amino-sugar Derivatives

The Action of Alkaline Reagents on 2 3-1 6- and 3 4-l 6-Dianhydro-3-talose. A Constitutional Synthesis of Chondrosamine and other Amino-Sugar Derivatives, S. P. James, F. Smith, M. Stacey, and L. F. Wiggins, J. Chem. Soc., (1946) 625-628. 

Pneumococcus, polysaccharides from, 6-7 Poly(a-L-guluronic acid), 353, 355-356,415 Poly(P-D-mannuronic acid), 353-354,414 Polysaccharides, 311 -439 amino sugar derivatives, 166 chemical repeating units, 321, 324-325... 

Raney Nickel was also used as the catalyst for the reduction of nitro sugars to amino sugars by hydrogenation.87 Under these conditions, nitro sugar 127 was reduced to amino sugar derivative 128, without removal of the benzyl protecting group. Compound 128 was finally converted into azepane 129 (Scheme 39).88... 

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. 

Glucosamine is an amino sugar derivative occurring naturally in healthy tendons, ligaments and cartilage. Its use has been shown to be effective in the symptomatic relief of osteoarthritis, especially in combination with chondroitin, also a derivative of cartilage. 

Being an amino sugar derivative, glucosamine should be used cautiously in patients with impaired glucose tolerance. Side-effects of glucosamine include nausea, abdominal pain and indigestion. 

Palladium-catalyzed, Allylic Amination. Allylic substitution of mono-saccharidic hex-2-enopyranoside 4-acetates with secondary amines in the presence of tetrakis (triphenylphosphine)palladium(O) liad led to a large variety of 4-aminated 2-enosides, with retention of configuration (56-58). The method was applied to the disaccaridic enoside 1 to give, with benzylmethylamine or dibenzylamine, the 4-amino sugar derivatives g in yields of 92 and 67% (46). Studies concerning hydrox-ylation of t)ie double bond and subsequent deprotection are incomplete. 

G. W.J. Fleet, Spec. Publ.-R. Soc. Chem. 65,149-162 (1988) Amino-Sugar Derivatives and Related Compounds as Glycosidase lnhibitors. ... 

Undoubtedly, the vicinal groups play a fundamental role in the outcome of this reaction, especially with the sugars, where the favored conformation of the molecule at equilibrium is controlled at the outset by groups that determine whether the molecule exists as a cyclic or acyclic structure. The deamination of cyclic and acyclic amino sugar derivatives by nitrous acid will be considered in turn. 

Dutcher, James D., Chemistry of tlie Amino Sugars Derived from Antibiotic Substances, 18, 259-308... 

Acetamidodeoxyhexoses. A further modification of the 4-keto-inter-mediate has been independently shown by Ashwell and by Strominger and associates (Table I, References 20, 21, 22, 23). Transamination reactions with L-glutamate as the amino donor and pyridoxal phosphate as coenzyme led to formation of 3-amino 3,6-dideoxy- and 4-amino 4,6-dideoxyhexoses, respectively. Acetylation with acetyl coenzyme A yields the naturally-occurring N-acetyl amino sugar derivatives. 

Alternate Protocol 2 Determination of Amino Sugar Derivatives Using the Morgan-Elson Method Reagents and Solutions Commentary... 

ALTERNATE DETERMINATION OF AMINO SUGAR DERIVATIVES USING THE PROTOCOL 2 MORGAN-ELSON METHOD... 

Amino sugar derivatives, Morgan-Elson detection method, 656-659 a-Amylase degradation, 716 in plant cell wall isolation, 706 in total starch determination, 685... 

C. A. Johnson and P. H. Gross, Heterocyclic amino sugar derivatives. 6. Stabilization of a reactive intermediate by steric hindrance. Mechanism of 3,6-anhydro sugar formation, J. Org. Chem., 38 (1973) 2509-2512. 

Azide ions are by far the most common nucleophilic species employed in substitution reactions for the preparation of amino sugars. An azido moiety is stable under many reaction conditions but can be reduced to an amino group by a variety of reagents. The nucleophilicity of azido ions can be increased by the addition of a suitable crown ether to complex the counterion.36c,63b In the past, ammonia and hydrazine were used as nucleophiles to overcome unfavourable dipolar interactions that arise when charged nucleophiles were used. However, a drawback of the use of these nucleophiles is that the product is still nucleophilic and can perform a second displacement. Phthalimide ions have successfully been applied in displacement reactions to yield a protected amino sugar derivative.58 63f... 

Application of Hudson s Isorotation Rides to 2-Amino Sugar Derivatives 267... 

The nomenclature of the glucosamine and chondrosamine derivatives referred to in this article is essentially that used in the literature. A few minor changes have been made in order to effect a greater uniformity and precision in the classification. No attempt has been made to introduce any new nomenclature of the 2-amino sugar derivatives. It is now accepted that they are more correctly designated as the 2-amino-2-deoxy-sugars. 

The Rf values of some amino sugar derivatives are shown in Table I. 

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