Amino sugar antibiotics

J. Jurczak and A. Golfbiowski, The synthesis of antibiotic amino sugars from a-amino aide hydes, Antibiotics and Antiviral Compounds, Chemical Synthesis and Modification, (K. Krohn, H. Kirst, and H. Maas, eds.), VCH, Weinheim, 1993, p. 343. 

Antibiotic Amino sugar present Formula Nonnitrogenxms sugars present Formula Disaccharides characterized FormuU... 

Aminoglycosides. Antibiotics ia the amiaoglycoside group characteristically contain amino sugars and deoxystreptamiae or streptamiae. This family of antibiotics has frequentiy been referred to as aminocyclitol amiaoglycosides. Representative members are streptomycia, neomycin, kanamycia, gentamicin, tobramycia, and amikacin. These antibiotics all inhibit proteia biosynthesis. 

Amino sugars, such as o-glucosamine, have an OH group leplaced by an -NH2. The N-acetyl amide derived from o-glucosamine is the monosaccharide unit from which chitm, the hard crust that protects insects and shellfish, is made. Still otheramino sugars are found in antibiotics such as streptomycin and gentamicin. 

The amino sugars include D-glucosamine, a constiment of hyaluronic acid (Figure 13-10), D-galactosamine (chondrosamine), a constituent of chondroitin and D-mannosamine. Several antibiotics (eg, erythromycin) contain amino sugars believed to be important for their antibiotic activity. 

The macrolide antibiotics are characterized by possessing molecular structures that contain large (12-16-membered) lactone rings linked through glycosidic bonds with amino sugars. 

The hydroxy groups in natural products like, for example, the macrolide antibiotics erythromycin, 1"1 and desmycosin, 2001 2011 as well as the 3-(hydroxymethyl)-2- or 3-cephems 2021 and derivatives of the amino sugar garamin 2031 have been converted into the carbamate function with CDI and amines. In the case of aminoglycoside antibiotics of the sisomicin series, thiocarbamates or dithiocarbamates have been prepared from alcohols or thiols using ImCSIm and amines.12041... 

The chemistry and biochemistry of nitro sugars and amino sugars have stimulated extensive research. They are the components of various antibiotics, which show important biological... 

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. 

Lincosamides (lincomycin and clindamycin) are representatives of a very small group of drugs synthesized up of an amino acid bound to an amino sugar. Lincosamides bind with the 50 S ribosomal subunit of bacteria and inhibit protein synthesis. They also inhibit pep-tidyltransferase action. Lincosamides are bacteriostatic antibiotics however, when they reach a certain level in the plasma, they also exhibit bactericidal action against some bacteria. Lincosamides are highly active against anaerobic infections such as Peptococcus, Peptostreptococcus, Actinomyces, Propionibacterium, and Clostridium fringens, a few types of Peptococcus and Clostridium. 

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]. 

The aminoglycosides are a closely related family of antibiotics produced almost exclusively by members of the genus Streptomyces and Micromonospora (Table 1.19). Most are polycationic compounds, composed of a cyclic amino alcohol to which amino sugars are attached. They all induce their bacteriocidal effect by inhibiting protein synthesis (apparently by binding to the 30 S and, to some extent, the 50 S, ribosomal subunits). Most are orally inactive, generally necessitating their parenteral administration. 

Carbohydrate antibiotics Antibiotics that contain one or more amino sugars within the molecule are called carbohydrate antibiotics. For example, gentamicin is composed of three different units purpurosamine, 2-deoxystreptamine and garosamine. Other examples include streptomycin and neomycin. 

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