The identification of cis-11,12-methylene-2-hydroxyoctadecanoic acid from Thiobacillus thiooxidans.
نویسندگان
چکیده
A polar fatty acid has been observed as a component of an ornithine-containing lipid of Thiobacillus thiooxidans. A comparison of thin layer chromatographic mobilities of reference compounds to those of the natural acid and its derivatives suggested that the acid was a 2-hydroxy fatty acid. The presence of a cyclopropane function in the acid was indicated by W-labeling experiments and infrared spectroscopy. Mass spectrometry of the methyl ester and the acetylated methyl ester of the natural acid provided a molecular weight for the acid. Equivalent chain lengths were determined for the natural acid, the acid obtained by oxidative decarboxylation of the natural acid with permanganate, and the acids derived through reductive ring cleavage of the cyclopropane group in the ester of the oxidatively decarboxylated natural acid. The mass spectral data, the equivalent chain length determinations, and the permanganate oxidation study clearly indicated that the acid possessed an 18carbon chain with a methylene bridge and a 2-hydroxyl function. The equivalent chain length determinations further suggested that the cyclopropane group had the cis configuration. Mass spectrographic analysis of the branched chain esters obtained by reductive cleavage of the ester which was in turn derived through oxidative decarboxylation of the natural acid allowed the assignment of the 11,12 position for the cyclopropane group. Based on these data, the polar acid is proposed to be cis-11,12-methylene-2hydroxyoctadecanoic acid.
منابع مشابه
The Identification of cis=ll ,l%Methylene=2=hydroxyoctadecanoic Acid from Thiobacillus thiooxidans*
A polar fatty acid has been observed as a component of an ornithine-containing lipid of Thiobacillus thiooxidans. A comparison of thin layer chromatographic mobilities of reference compounds to those of the natural acid and its derivatives suggested that the acid was a 2-hydroxy fatty acid. The presence of a cyclopropane function in the acid was indicated by W-labeling experiments and infrared ...
متن کاملThe Identification of cis-II, I2-Methylene-2-hydroxyoctadecanoicAcid from Thiobacillus thiooxidans
متن کامل
The structure of an ornithine-containing lipid from Thiobacillus thiooxidans.
The structure of an ornithine-containing lipid from Z’Gobacillus fhiooxidans has been elucidated. Methanolysis of the lipid released methyl cis-ll,lZ-methylene-Z-hydroxyoctadecanoate. Acid hydrolysis of the residue yielded ornithine and a mixture of fatty acids, the major components of which were 3-hydroxyhexadecanoic and 2-hexadecenoic acids. Identification of the 3-hydroxy fatty acid was base...
متن کاملA simple medium modification for isolation, growth and enumeration of Acidithiobacillus thiooxidans (syn. Thiobacillus thiooxidans) from water samples.
High concentrations of H(2)S in groundwater are commonly removed using Biological Trickling Filter (BTF) that contains high numbers of biofilm immobilized sulfur oxidizing bacteria (mainly Thiobacillus thiooxidans). BTF performance requires continuous monitoring of these bacteria at several sampling points. The Most Probable Number (MPN) technique is at the moment the method of choice to enumer...
متن کاملEffect of pH on sulfite oxidation by Thiobacillus thiooxidans cells with sulfurous acid or sulfur dioxide as a possible substrate.
The oxidation of sulfite by Thiobacillus thiooxidans was studied at various pH values with changing concentrations of potassium sulfite. The optimal pH for sulfite oxidation by cells was a function of sulfite concentrations, rising with increasing substrate concentrations, while that by the cell extracts was unaffected. The sulfite oxidation by cells was inhibited at high sulfite concentrations...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- The Journal of biological chemistry
دوره 244 17 شماره
صفحات -
تاریخ انتشار 1969