| Trapping of transiently formed quinone methide during enzymatic conversion of N-acetyldopamine to N-acetylnorepinephrine. | |
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MedLine Citation:
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PMID: 2503395 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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We have demonstrated that quinone methide formation is an important aspect of insect physiology and proposed that enzymatically generated quinone methides react nonenzymatically with water or other nucleophiles to form Michael-1,6-addition products [(1988) Adv. Insect Physiol. 21, 179-231; (1989) J. Cell. Biochem. suppl. 13C, 58]. Using a purified o-quinone isomerase from the larval cuticle of Sacrophaga bullata and mushroom tyrosinase, we now demonstrate that transiently formed N-acetyldopamine quinone methide from N-acetyldopamine can be trapped by methanol to produce beta-methoxy N-acetyldopamine. The methanol adduct thus formed was found to be a racemic mixture and can be resolved into the optical isomers on cyclodextrin chiral column. These results confirm our contention that enzymatically generated quinone methides are nonenzymatically and nonstereoselectively transformed to Michael-1,6-adducts by reaction with water or other nucleophiles. |
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Authors:
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M Sugumaran; S Saul; V Semensi |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: FEBS letters Volume: 252 ISSN: 0014-5793 ISO Abbreviation: FEBS Lett. Publication Date: 1989 Jul |
Date Detail:
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Created Date: 1989-09-21 Completed Date: 1989-09-21 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 0155157 Medline TA: FEBS Lett Country: NETHERLANDS |
Other Details:
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Languages: eng Pagination: 135-8 Citation Subset: IM |
Affiliation:
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Department of Biology, University of Massachusetts, Boston 02125. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Chemical Phenomena Chemistry Chromatography, High Pressure Liquid Dopamine / analogs & derivatives*, metabolism Insects / enzymology, metabolism Isomerases / metabolism Monophenol Monooxygenase / metabolism Norepinephrine / analogs & derivatives*, metabolism Quinones / metabolism* Spectrophotometry, Ultraviolet |
| Grant Support | |
ID/Acronym/Agency:
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2RO1-AI-14753/AI/NIAID NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Quinones; 2494-12-4/N-acetyldopamine; 30959-88-7/N-acetylnorepinephrine; 51-41-2/Norepinephrine; EC 1.14.18.1/Monophenol Monooxygenase; EC 5.-/Isomerases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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