Studies on the biosynthesis of the m-C/sub 7/N unit in the antibiotics manumycin and asukamycin
The manumycin group of antibiotics, represented by manumycin (1), asukamycin (2), colabomycin, U-62,162, and U-56,407, contains as a central structural element a multifunctional m-C/sub 7/N unit. This moiety, consisting of a six-membered ring carrying one carbon and one nitrogen atom in a meta disposition, is ubiquitous in nature in a variety of forms. The m-C/sub 7/N unit is most commonly quininoid as exemplified by the rifamycins, mitomycins, and ansamitocins, or aromatic as in the case of pactamycin. In these antibiotics, its biogenesis has been demonstrated to proceed by a branch of the shikimic acid pathway, ultimately via 3-amino-5-hydroxybenzoic acid (AHBA) or 3-aminobenzoic acid (ABA). Other forms of the m-C/sub 7/N unit are found in the valienamine moiety of validamycin and acarbose and in the antibiotic kinamycin; in these cases it has been shown that the unit derives from intermediates of the pentose phosphate pathway and from acetate, respectively. The structural and stereochemical uniqueness observed in 1 (4R) and 2 (4S) led the authors to study the biosynthesis of these antibiotics in parallel. In this communication they present confirming a new biochemical pathway leading to the m-C/sub 7/N unit.
- Research Organization:
- Ohio State Univ., Columbus (USA)
- OSTI ID:
- 6220629
- Journal Information:
- J. Am. Chem. Soc.; (United States), Vol. 110:13
- Country of Publication:
- United States
- Language:
- English
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ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
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CARBON COMPOUNDS
BIOSYNTHESIS
NITROGEN COMPOUNDS
ANTIBIOTICS
EXPERIMENTAL DATA
STRUCTURAL CHEMICAL ANALYSIS
ANTI-INFECTIVE AGENTS
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DRUGS
INFORMATION
NUMERICAL DATA
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550500 - Metabolism