| Preparation of 7-hydroxy-2-oxoindolin-3-ylacetic acid and its [13C2], [5-n-3H], and [5-n-3H]-7-O-glucosyl analogues for use in the study of indol-3-ylacetic acid catabolism. | |
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MedLine Citation:
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PMID: 11540898 Owner: NASA Status: MEDLINE |
Abstract/OtherAbstract:
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An improved synthesis of 7-hydroxy-2-oxoindolin-3-ylacetic acid via the base-induced condensation reaction between oxalate esters and 7-benzyloxyindolin-2-one is described. 7-Benzyloxyindolin-2-one was prepared in four steps and 50% overall yield from 3-hydroxy-2-nitrotoluene. The yield of the title compound from 7-benzyloxyindolin-2-one was 56%. This route was used to prepare 7-hydroxy-2-oxoindolin-3-yl[13C2]acetic acid in 30% yield from [13C2]oxalic acid dihydrate. The method could not be extended to the preparation of the corresponding [14C2]-compound. However, an enzyme preparation from Zea mays roots catalysed the conversion of carrier-free [5-n-3H]indol-3-ylacetic acid with a specific activity of 16.7 Ci mmol-1 to a mixture of 7-hydroxy-2-oxo[5-n-3H]indolin-3-ylacetic acid and its [5-n-3H]-7-O-glucoside in ca. 3 and 40% radiochemical yield respectively. The glucoside was converted into the 7-hydroxy compound in 80% yield by means of beta-glucosidase. |
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Authors:
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P Lewer |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Journal of the Chemical Society. Perkin transactions 1 Volume: 1987 ISSN: 0300-922X ISO Abbreviation: J. Chem. Soc. Perkin Trans. I Publication Date: 1987 Apr |
Date Detail:
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Created Date: 1998-08-28 Completed Date: 1998-08-28 Revised Date: 2009-06-08 |
Medline Journal Info:
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Nlm Unique ID: 7505598 Medline TA: J Chem Soc Perkin 1 Country: ENGLAND |
Other Details:
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Languages: eng Pagination: 753-7 Citation Subset: S |
Affiliation:
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Department of Botany and Plant Pathology, Michigan State University, East Lansing 48824-1312, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Hydroxyindoleacetic Acid
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analogs & derivatives*,
chemical synthesis,
metabolism Indoleacetic Acids / metabolism* Plant Growth Regulators / metabolism* Plant Roots / metabolism Zea mays / metabolism* |
| Chemical | |
Reg. No./Substance:
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0/Indoleacetic Acids; 0/Plant Growth Regulators; 54-16-0/Hydroxyindoleacetic Acid; 87-51-4/indoleacetic acid; 95061-84-0/7-hydroxy-2-oxoindole-3-acetic acid 7'-O-glucopyranoside |
| Investigator | |
Investigator/Affiliation:
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R S Bandurski / MI St U, East Lansing |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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