## Abstract A method for the production of carboxy‐labelled l‐carnitine is described. The first step is the chemical synthesis of 4‐N‐trimethylammoniobutanoate (butyrobetaine) from the precursors 4‐aminobutanoate and iodomethane. The second step involves the hydroxylation of butyrobetaine to form l
Synthesis of radioactively methyl-labelled (l)-carnitine
✍ Scribed by Stephen T. Ingalls; Charles L. Hoppel; Julia S. Turkaly
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- French
- Weight
- 295 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
Commercial (l)‐carnitine chloride was N‐demethylated by the action of sodium benzenemercaptide in warm N,N‐dimethylformamide. The product 4‐(N,N‐dimethylammonio)‐3‐hydroxybutanoic acid chloride salt was isolated in good yield by ion exchange chromatography. Methylation of the product by ^14^C ‐iodomethane in dry methanol produced biologically active 4‐N‐ Me‐^14^C ‐(l)‐carnitine chloride of high specific activity in excellent yield.
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The two geometrical isomers o f B-methyl s t y r e n e oxide were synthesized by a sequence o f r e a c t i o n s which l e d t o stereochemic a l l y pure products, and o b v i a t e d any need t o separate t h e isomers.
A route to 'lc-labelled (R) -carnithe (1) , based on the methylation of the dimethyl derivative ( 2 ) is described. Furthermore, a five-step synthesis for the enantiomerically pure precursor ( 2 ) is outlined. 0362 -4803/91/050599 -08W5.00 ' i j 1991 by John Wiley & Sons. Ltd.
## Abstract Fluoride‐directed methylation of the aryl hydroxyl of hydroxyphenyl glycosides with radioactive methyl iodide allows the incorporation of label under mild conditions that preserve the glycosidic link. The effectiveness of this approach has been demonstrated by the synthesis of two ^14^C
A rapid method for the preparation of [ I-'4C]acetyl-~-carnitine is described. The method involves exchange of [ I-'%]acetic acid into a pool of unlabeled acetyl-L-carnitine using the enzymes acetyl-CoA synthetase and carnitine acetyltransferase. After isotopic equilibrium is attained, radioactive a
The causes of carnitine deficiency syndromes are not completely understood, but decomposition of L-carnitine in vivo is likely t o be involved. Carnitine is metabolized to y-butyrobetaine, and crotonobetaine is probably an intermediate in this pathway. To validate experimentally the precursor-produc