Bioconversion of 1-adamantanol to 1,3-adamantanediol using Streptomyces sp. SA8 oxidation system.
To efficiently produce 1,3-adamantanediol (1,3-ad(OH)(2)) from 1-adamantanol (1-adOH), our stocks of culture strains and soil microorganisms were surveyed for hydroxylation activity towards 1-adOH. Among them, the soil actinomycete SA8 showing the highest hydroxylation activity was identified as Streptomyces sp. based on 16S ribosomal DNA sequence analysis. The reaction products were purified by silica gel column chromatography, and from NMR and MS analyses, they were identified as 1,3-ad(OH)(2) and 1,4-ad(OH)(2). Streptomyces sp. SA8 produced 5.9 g l(-1) 1,3-ad(OH)(2)from 6.2 g l(-1) 1-adOH in culture broth after 120 h at 25 degrees C. Using resting cells, 2.3 g l(-1) 1,3-ad(OH)(2) was produced after 96 h of incubation at a 69% conversion rate. In both cases, 1,4-ad(OH)(2) was formed as a byproduct at a rate of about 15%. Strain SA8 also hydroxylated 2-adamantanol and 2-methyl-2-adamantanol.
Mitsukura
Koichi
K
Department of Biomolecular Science, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. mitukura@gifu-u.ac.jp
Sakamoto
Hiromu
H
Kubo
Haruka
H
Yoshida
Toyokazu
T
Nagasawa
Toru
T
D000218:Adamantane / Q000031:analogs & derivatives* / Q000378:metabolism; D006900:Hydroxylation; D010084:Oxidation-Reduction; D017422:Sequence Analysis, DNA; D013302:Streptomyces / Q000235:genetics / Q000378:metabolism*; D013379:Substrate Specificity
C550825:1,3-adamantanediol; C434445:1-adamantanol; D000218:Adamantane