Isolation of a new antibiotic, alaremycin, structurally related to 5-aminolevulinic acid from Streptomyces sp. A012304.
A new antibiotic, which is structurally related to 5-aminolevulinic acid, a precursor of heme biosynthesis, and named alaremycin, was isolated from the culture broth of an actinomycete strain through a random screening with the blue assay to detect the formation of anucleate cells in Escherichia coli. The producing strain was identified as Streptomyces sp. by morphological, physiological, chemical and genetic criteria. Alaremycin was purified from the culture supernatant by HP-20 hydrophobic-interaction chromatography, sequential solvent/water extraction in the acidic or alkaline pH range, and QMA cation-exchange chromatography. The chemical structure of alaremycin was determined as 5-acetamido-4-oxo-5-hexenoic acid by analyses of mass and NMR spectra. The antibacterial activity of alaremycin was enhanced in the presence of 5-aminolevulinic acid.
Awa
Yuuki
Y
Department of Bioengineering, Tokyo Institute of Technology, Yokohama 226-8501, Japan.
Iwai
Noritaka
N
Ueda
Tomohiko
T
Suzuki
Kenji
K
Asano
Shoji
S
Yamagishi
Jun-ichi
J
Nagai
Kazuo
K
Wachi
Masaaki
M
D000614:Aminocaproates / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000622:Aminolevulinic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D013302:Streptomyces / Q000737:chemistry* / Q000145:classification / Q000378:metabolism
D000614:Aminocaproates; D000900:Anti-Bacterial Agents; C506902:alaremycin; D000622:Aminolevulinic Acid