Studies on the biosynthesis of the m-C/sub 7/N unit in the antibiotics manumycin and asukamycin

Journal Article · Wed Jun 22 04:00:00 EDT 1988 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00221a066· OSTI ID:6220629

Beale, J M; Herrold, R E; Floss, H G; Thiericke, R; Zeeck, A; Nakagawa, A; Omura, S

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), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 110:13; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
550500 -- Metabolism
59 BASIC BIOLOGICAL SCIENCES
ANTI-INFECTIVE AGENTS
ANTIBIOTICS
BIOSYNTHESIS
CARBON COMPOUNDS
DATA
DRUGS
EXPERIMENTAL DATA
INFORMATION
NITROGEN COMPOUNDS
NUMERICAL DATA
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS