Amino derived from antibiotic substances

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

Durette, Philippe L., and Horton, D Conformational Analysis of Sugars and Their Derivatives, 26,49-125 Dutcher, James D., Chemistry of the Amino Sugars Derived from Antibiotic Substances, 18, 259-308... 

CHEMISTRY OF THE AMINO SUGARS DERIVED FROM ANTIBIOTIC SUBSTANCES... 

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. 

Molecules of type I are the classical product of reactions between monofunctional reactants. In many cases, they can be considered to be derived from the functionalization of a substrate or, reciprocally, of an amine, in order to attach chemical moieties purposely designed for specific uses, without substantially affecting the essential molecular structure. This is the case, for instance, of the antibiotic substance 494, which assumes hydrophilic properties upon aminomethylation of the pharmacologically active substrate having an amino acidic residue, or of the complexant agent 495,- as well as of the polyacrylamide Mannich base 502. - ... 

Penicillins and cephalosporins are charaeterized by (3-lactam structures and are the antibiotics that have traditionally been those most eommonly used in the treatment of infeetions. Pharmaceutical companies have synthesized a variety of semisynthetic (3-lactam compounds for use as oral antibiotics, for example, ampicillin and amoxieillin. These penicillin derivatives are prepared by aeylation of 6-amino-penicillanie acid (6-APA) derived from penicillin G (benzyl penicillin) or penicillin V (phenoxymethyl penicillin). An immobilized penicillin amidase (penicillin acylase) from Escherichia coli or Bacillus megaterium is used to prepare the 6-APA in nearly quantitative yield (Fig. 4). This substance is used as the starting material for the produetion of a number of other penieillins. The immobilized enzyme can be reused more than... 

Alkaloids represent one of the largest class of natural products with over 12000 defined structures [1], They can be summarized as nitrogen containing, mostly N-heterocyclic substances whose carbon skeleton is derived from amino acids. In a broader definition this group includes proto- and pseudoalkaloids and a number of microbial metabolites that are usually classified as antibiotics. In this review a broad definition of what to consider an alkaloid was chosen, albeit the emphasis is on alkaloids sensu strictu. 

In the 26 years since the discovery of tyrothricin—the first peptide antibiotic isolated—more than a hundred antibiotic substances containing one or more amino acids or moieties derived from amino acids have been described. However, despite considerable efforts, the structures of relatively few peptide antibiotics have been determined and ultimately proved by synthesis. There are several reasons for this. 

Similarities in structure commonly reflect similarities in biogenesis. Consideration of the architectural patterns and structural relationships of natural products enabled Collie, Robinson, Ruzicka and others to discern the biogenetic units from which certain phenolic compounds, alkaloids and terpenes were formed. A survey of the antibiotics indicates that one large collection of these substances can be derived mainly from amino acid residues, another mainly from acetate (or, on occasion, propionate) and a third from simple sugars. Some structures can be dissected into two or more different fragments that are derived from different types of biogenetic unit. 

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