Document Detail

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.
MedLine Citation:
PMID:  11540898     Owner:  NASA     Status:  MEDLINE    
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.
P Lewer
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
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:
Created Date:  1998-08-28     Completed Date:  1998-08-28     Revised Date:  2009-06-08    
Medline Journal Info:
Nlm Unique ID:  7505598     Medline TA:  J Chem Soc Perkin 1     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  753-7     Citation Subset:  S    
Department of Botany and Plant Pathology, Michigan State University, East Lansing 48824-1312, USA.
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MeSH Terms
Hydroxyindoleacetic Acid / analogs & derivatives*,  chemical synthesis,  metabolism
Indoleacetic Acids / metabolism*
Plant Growth Regulators / metabolism*
Plant Roots / metabolism
Zea mays / metabolism*
Reg. No./Substance:
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
R S Bandurski / MI St U, East Lansing

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