Document Detail


Synthesis of the 1-monoester of 2-ketoalkanedioic acids, for example, octyl α-ketoglutarate.
MedLine Citation:
PMID:  23163977     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Oxidative cleavage of cycloalkene-1-carboxylates, made from the corresponding carboxylic acids, and subsequent oxidation of the resulting ketoaldehyde afforded the important 1-monoesters of 2-ketoalkanedioic acids. Thus ozonolysis of octyl cyclobutene-1-carboxylate followed by sodium chlorite oxidation afforded the 1-monooctyl 2-ketoglutarate. This is a cell-permeable prodrug form of α-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right.
Authors:
Michael E Jung; Gang Deng
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2012-11-28
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  77     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Dec 
Date Detail:
Created Date:  2012-12-11     Completed Date:  2013-06-17     Revised Date:  2014-07-16    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  11002-5     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Carboxylic Acids / chemistry*
Cycloparaffins / chemistry*
Esters
Ketoglutaric Acids / chemistry*
Molecular Structure
Grant Support
ID/Acronym/Agency:
S10 RR025631/RR/NCRR NIH HHS; S10RR025631/RR/NCRR NIH HHS
Chemical
Reg. No./Substance:
0/Carboxylic Acids; 0/Cycloparaffins; 0/Esters; 0/Ketoglutaric Acids; 328-50-7/alpha-ketoglutaric acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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