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Synthesis of 4,4-Disubstituted L-Glutamic Acids by Enzymatic Transamination

✍ Scribed by Virgil Hélaine; Joël Rossi; Thierry Gefflaut; Sébastien Alaux; Jean Bolte

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 97 KB
Volume: 343
Category: Article
ISSN: 1615-4150
DOI: 10.1002/1615-4169(200108)343:6/7<692::aid-adsc692>3.0.co;2-6

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ChemInform Abstract: Synthesis of 4,4-Di

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A New Access to Alkyl-α-ketoglutaric Acids, Precursors of Glutamic Acid Analogues by Enzymatic Transamination. Application to the Synthesis of (2S,4R)-4-Propyl-glutamic Acid. -The new ketoglutarate (V) is easily available by a novel route via Claisen-Johnson rearrangement of ester (I) with orthoest

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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

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ChemInform Abstract: Stereoselective Synthesis of 2,3-Disubstituted Glutamic Acid Derivatives by Conjugate Addition to 3,4-Didehydropyroglutamates.

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Synthesis of L-glutamic acid stereospeci

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## Abstract 4‐[^2^H~2~]‐L‐glutamic acid was prepared in excellent yield by enzymatic reductive amination of 4‐[^2^H~2~]‐2‐ketoglutaric acid. The synthesis of stereospecifically deuterated (4 R) and (4 S)‐[4‐^2^H~2~]‐L‐glutamic acids from (2 RS, 4 S) and (2 RS, 4 R)‐4‐hydroxyglutamic acids, involvin