Enzymatic separation of cis and trans isomers of alicyclic alcohols
| Autor: | Akella Chendrasekhar, Barbara N. Alberti, Alexander M. Klibanov |
|---|---|
| Rok vydání: | 1983 |
| Předmět: |
chemistry.chemical_classification
biology Stereochemistry Phosphatase Substituent Acid phosphatase Bioengineering Alkaline hydrolysis (body disposal) Applied Microbiology and Biotechnology Biochemistry chemistry.chemical_compound Alicyclic compound chemistry biology.protein Alkaline phosphatase Cis–trans isomerism Biotechnology Methyl group |
| Zdroj: | Enzyme and Microbial Technology. 5:265-268 |
| ISSN: | 0141-0229 |
| DOI: | 10.1016/0141-0229(83)90075-3 |
| Popis: | It has been discovered that phosphatases [alkaline phosphatase, orthophosphoric-monoester phosphohydrolase (alkaline optimum), EC 3.1.3.1, and acid phosphatase, orthophosphoric-monoester phosphohydrolase (acid optimum), EC 3.1.3.2] display a remarkable geometric specificity in the hydrolysis of cis and trans isomers of monoorthophosphate esters of substituted alicy clicalcohols. While steric hindrances prevent potato acid phosphatase from hydrolysing cis -2-methylcyclohexyl and cis -2-methylcyclopentyl phosphates, the corresponding trans isomers are readily hydrolysed by the enzyme (non-enzymatic, acid-catalysed or base-catalysed hydrolyses of the cis and trans isomers occur at similar rates). Cis isomers of methylcyclohexyl phosphates, in which the methyl group is remote from the hydrolysed ester bond, 3- or 4-, have nearly the same reactivities to phosphatases as their trans counterparts . However, if the methyl group in position 4 is replaced by a bulky substituent, e.g. tert-butyl, phosphatases again hydrolyse only the trans and not the cis isomer. These phenomena afford a simple method for preparative separation of cis and trans isomers of alicyclic alcohols: a mixture of the isomers is first phosphorylated with POCl 3 and then hydrolysed by phosphatase. The trans alcohol formed is extracted with CCl 4 , followed by alkaline hydrolysis of the remaining cis -tester and subsequent extraction of the cis alcohol produced. |
| Databáze: | OpenAIRE |
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