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Asymmetric synthesis of L-[4-13C]glutamic acid and glutamine

โœ Scribed by Kazuhiko Takatori; Takuya Sakamoto; Masahiro Kajiwara

Publisher
John Wiley and Sons
Year
2006
Tongue
French
Weight
123 KB
Volume
49
Category
Article
ISSN
0022-2135

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โœฆ Synopsis

l-[4-l3 C]Glutamic acid (1) and l-[4-13 C]glutamine (2) were synthesized from sodium [2-13 C]acetate (5) and Dellaria's oxazinone 3 as a chiral glycine equivalent. Sodium [2-13 C]acetate (5) was converted to [2-13 C]acrylate 4. Diastereoselective Michael addition of the enolate of 3 to the acrylate 4 proceeded with high diastereoselectivity to give the adduct 12. Reductive cleavage of the C-S bond, ethanolysis, hydrogenolysis and hydrolysis gave l-[4-13 C]glutamic acid (1). l-[4-13 C]Glutamine (2) was synthesized from 1 in 4 steps.

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