✦ LIBER ✦

Stable isotope labeled alpha-ketoacids

✍ Scribed by Sun-Shine Yuan; Alfred M. Ajami

Publisher: John Wiley and Sons
Year: 1984
Tongue: French
Weight: 288 KB
Volume: 21
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580210807

No coin nor oath required. For personal study only.

✦ Synopsis

A l k y l a t i o n o f d i e t h y l oxalpropionate w i t h [

D3]methyl i o d i d e f o l l o w e d by a c i d h y d r o l y s i s l e d t o 3-[D3]methyl-2-oxobutyric ( a -k e t o i s o v a l e r i c ) acid. A l k y l a t i o n o f N -t -b u t y l p r o p y l i m i n e w i t h [D3]methyl i o d i d e f o l l o w e d by h y d r o l y s i s gave 2-[D3]methylpropanal. T h i s was f u r t h e r a l k y l a t e d w i t h 2,2d i f 1 uoro-1 -t o s y l oxyvinyl 1 i t h i um and hydrolyzed t o a f f o r d 4-[D31methyl -2-0x0pentanoic ( a -k e t o i s o c a p r o i c ) acid. D i a z o t i z a t i o n o f [l-C l l e u c i n e e t h y l e s t e r w i t h t -b u t y l n i t r i t e f o l l o w e d by peracid o x i d a t i o n and h y d r o l y s i s gave [l-Cl4methyl-2-oxopentanoic acid. I n each case, t h e a -k e t o a c i d s were i s o l a t e d as sodium s a l t s .

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