Factors affecting the normal and branched-chain acyl moieties of teicoplanin components produced by Actinoplanes teichomyceticus

• Published in: Journal of general microbiology Vol. 137; no. 3; pp. 587 - 592
• Main Authors: Borghi, Angelo, Edwards, Duncan, Zerilli, Luigi Franco, Lancini, Gian Carlo
• Format: Journal Article
• Language: English
• Published: London Soc General Microbiol 01.03.1991; New York, NY Cambridge University Press
• Subjects: Acylation; amino acids; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - metabolism; Antibiotics (antibacterial agents, antifungal agents); Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; Applied microbiology; Bacteria, Aerobic - metabolism; Biological and medical sciences; Chromatography, High Pressure Liquid; Fatty Acids - metabolism; Fundamental and applied biological sciences. Psychology; Gas Chromatography-Mass Spectrometry; Glycopeptides - chemistry; Glycopeptides - metabolism; glycoproteins; Gram-Positive Bacteria - metabolism; Microbiology; Molecular Structure; Oxidation-Reduction; peptide antibiotics; Protein Precursors - metabolism; Teicoplanin; Culture medium; Gas chromatography; Antibiotic; Glycopeptide; Aminoacid; Environmental factor; Biosynthesis; Antibacterial agent; Metabolism; Fatty acids; Mass spectrometry; Acylation
• ISSN: 0022-1287
• DOI: 10.1099/00221287-137-3-587

MMDRI, Lepetit Research Centre, Via R. Lepetit 34, 21040 Gerenzano (VA), Italy ABSTRACT Teicoplanin, a glycopeptide antibiotic produced by Actinoplanes teichomyceticus , comprises five main components, denoted T-A2 to T-A2-5, differing in the structure of their acyl side chain, which is linear in T-A2-1 and T-A2-3 and branched in the other components. Production of T-A2-1, characterized by a linear C10:1 acyl moiety, is entirely dependent on the presence of linoleate in the fermentation medium. Addition to the medium of oleic acid esters at 2 g l -1 increases the yields of T-A2-3, characterized by a linear C10:0 acyl chain, about threefold. The antibiotic linear side chains thus appear to originate from C18 unsaturated acid by β-oxidation degradation. The percentage of T-A2-2, T-A2-4 and T-A2-5, bearing the iso-C10:0, anteiso-C11:0 and iso-C11:0 acyl moieties, respectively, is strongly influenced by the presence in the medium of the amino acids known to be precursors of branched-chain fatty acids. Thus, valine increases the production of T-A2-2 whereas isoleucine or leucine increase the relative yields of T-A2-4 or T-A2-5, respectively. Analysis of the total cell lipids upon addition of the same amino acid shows corresponding increases in the proportion of the iso-C16:0, iso-C15:0 or anteiso-C17:0. A mutant A. teichomyceticus strain, which produces a novel teicoplanin with a linear C9:0 chain, differs from the wild strain in the presence of the linear C17:1 acid in its lipids. The relative incorporation of [ 14 C]acetate into teicoplanin acyl moieties is substantially lower when this precursor is added to grown A. teichomyceticus mycelium rather than at the time of inoculation. The results suggest that teicoplanin branched acyl moieties also originate from β-oxidation degradation of cellular long-chain fatty acids. Present Address: Farmitalia Carlo Erba Research Labs, Via C. Imbonate 14, 20159 Milano, Italy