Abstract
During the course of the purification of novel stereospecific secondary aklylsulphohydrolases present in certain detergent-degrading micro-organisms, it became apparent that substrates prepared by sulphating secondary alcohols with H2SO4 are heterogeneous. Apart from the racemization that occurs if resolved alcohols are sulphated, evidence is provided to show that other isomers are produced in which the position of the ester sulphate group on the alkyl chain has been altered. These changes can be avoided if pyridine/SO3 reagent (prepared with SO3) is substituted as sulphating agent. Experiments in which secondary alkyl sulphates prepared by both methods were tested as potential substrates for the two secondary alkylsulphohydrolase enzymes of Comamonas terrigena have provided initial information about the specificity of the enzymes.
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- Bartholomew B., Dodgson K. S., Matcham G. W., Shaw D. J., White G. F. A novel mechanism of enzymic ester hydrolysis. Inversion of configuration and carbon-oxygen bond cleavage by secondary alkylsulphohydrolases from detergent-degrading micro-organisms. Biochem J. 1977 Sep 1;165(3):575–580. doi: 10.1042/bj1650575. [DOI] [PMC free article] [PubMed] [Google Scholar]
- DODGSON K. S. Determination of inorganic sulphate in studies on the enzymic and non-enzymic hydrolysis of carbohydrate and other sulphate esters. Biochem J. 1961 Feb;78:312–319. doi: 10.1042/bj0780312. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Dodgson K. S., Fitzgerald J. W., Payne W. J. Chemically defined inducers of alkylsulphatases present in Pseudomonas C12B. Biochem J. 1974 Jan;138(1):53–62. doi: 10.1042/bj1380053. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Fitzgerald J. W. Secondary alkylsulphatases in a strain of Comamonas terrigena. Biochem J. 1975 Aug;149(2):477–480. doi: 10.1042/bj1490477. [DOI] [PMC free article] [PubMed] [Google Scholar]
- HSU Y. C. DETERGENT (SODIUM LAURYL SULPHATE)-SPLITTING ENZYME FROM BACTERIA. Nature. 1963 Dec 14;200:1091–1092. doi: 10.1038/2001091b0. [DOI] [PubMed] [Google Scholar]
- LLOYD A. G., TUDBALL N., DODGSON K. S. Infrared studies on sulphate esters. III. O-Sulphate esters of alcohols, amino alcohols and hydroxylated amino acids. Biochim Biophys Acta. 1961 Sep 30;52:413–419. doi: 10.1016/0006-3002(61)90397-3. [DOI] [PubMed] [Google Scholar]
- Matcham G. W., Dodgson K. S. Purification, properties and cellular localization of the stereospecific CS2 secondary alkylsulphohydrolase of Comamonas terrigena. Biochem J. 1977 Dec 1;167(3):723–729. doi: 10.1042/bj1670723. [DOI] [PMC free article] [PubMed] [Google Scholar]
- PAYNE W. J., FEISAL V. E. Bacterial utilization of dodecyl sulfate and dodecyl benzene sulfonate. Appl Microbiol. 1963 Jul;11:339–344. doi: 10.1128/am.11.4.339-344.1963. [DOI] [PMC free article] [PubMed] [Google Scholar]
- REES D. A. A NOTE ON THE CHARACTERIZATION OF CARBOHYDRATE SULPHATES BY ACID HYDROLYSIS. Biochem J. 1963 Aug;88:343–345. doi: 10.1042/bj0880343. [DOI] [PMC free article] [PubMed] [Google Scholar]