Journal article
Benzylic alcohols as stereospecific substrates and inhibitors for aryl sulfotransferase
Chirality (New York, N.Y.), Vol.3(2), pp.104-111
1991
DOI: 10.1002/chir.530030205
PMID: 1863522
Abstract
Aryl sulfotransferase IV catalyzes the 3′‐phosphoadenosine‐5′‐phosphosulfate (PAPS)‐dependent formation of sulfuric acid esters of benzylic alcohols. Since the benzylic carbon bearing the hydroxyl group can be asymmetric, the possibility of stereochemical control of substrate specificity of the sulfotransferase was investigated with benzylic alcohols. Benzylic alcohols of known stereochemistry were examined as potential substrates and inhibitors for the homogeneous enzyme purified from rat liver. For 1‐phenylethanol, both the (+)‐(R)‐and (−)‐(S)‐enantiomers were substrates for the enzyme, and the kcat/Km value for the (−)‐(S)‐enantiomer was twice that of the (+)‐(R)‐enantiomer. The enzyme displayed an absolute stereospecificity with ephedrine and pseudoephedrine, and with 2‐methyl‐1‐phenyl‐1‐propanol; that is, only (−)‐(1R,2S)‐ephedrine, (−)‐(1R,2R)‐pseudoephedrine, and (−)‐(S)‐2‐methyl‐1‐phenyl‐1‐propanol were substrates for the sulfotransferase. In the case of 1,2,3,4‐tetrahydro‐1‐naphthol, only the (−)‐(R)‐enantiomer was a substrate for the enzyme. Both (+)‐(R)‐2‐methyl‐1‐phenyl‐1‐propanol and (+)‐(S)‐1,2,3,4‐tetrahydro‐1‐naphthol were competitive inhibitors of the aryl sulfotransferase‐catalyzed sulfation of 1‐naphthalenemethanol. Thus, the configuration of the benzylic carbon bearing the hydroxyl group determined whether these benzylic alcohols were substrates or inhibitors of the rat hepatic aryl sulfotransferase IV. Furthermore, benzylic alcohols such as (+)‐(S)‐1,2,3,4‐tetrahydro‐1‐naphthol represent a new class of inhibitors for the aryl sulfotransferase. Copyright © 1991 Wiley‐Liss, Inc.
Details
- Title: Subtitle
- Benzylic alcohols as stereospecific substrates and inhibitors for aryl sulfotransferase
- Creators
- Satish I. Rao - University of IowaMichael W. Duffel - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Chirality (New York, N.Y.), Vol.3(2), pp.104-111
- Publisher
- Alan R. Liss, Inc
- DOI
- 10.1002/chir.530030205
- PMID
- 1863522
- ISSN
- 0899-0042
- eISSN
- 1520-636X
- Number of pages
- 8
- Language
- English
- Date published
- 1991
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984303284302771
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