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Stable isotope labeled alpha‐ketoacids
Author(s) -
Yuan SunShine,
Ajami Alfred M.
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210807
Subject(s) - chemistry , hydrolysis , methyl iodide , alkylation , iodide , acid hydrolysis , ethyl iodide , sodium iodide , alkaline hydrolysis , organic chemistry , catalysis
Alkylation of diethyl oxalpropionate with [D 3 ]methyl iodide followed by acid hydrolysis led to 3‐[D 3 ]methyl‐2‐oxobutyric (α‐ketoisovaleric) acid. Alkylation of N‐t‐butylpropylimine with [D 3 ]methyl iodide followed by hydrolysis gave 2‐[D 3 ]methylpropanal. This was further alkylated with 2,2‐difluoro‐1‐tosyloxyvinyllithium and hydrolyzed to afford 4‐[D 3 ]methyl‐2‐oxopentanoic (α‐ketoisocaproic) acid. Diazotization of [1‐ 13 C]leucine ethyl ester with t‐butylnitrite followed by peracid oxidation and hydrolysis gave [1‐ 13 C]4‐methyl‐2‐oxopentanoic acid. In each case, the α‐ketoacids were isolated as sodium salts.