Efficient Synthesis of γ-Oxo-and γ-Hydroxy-α-amino Acids. -Reduction of aminoester (Va) with Zn(BH 4 ) 2 permits intermediate isolation of the γ-hydroxy derivative, which is converted to lactone (IX) during silica gel chromatography. -(MERLA, B.;
ChemInform Abstract: Kynureninase in Organic Synthesis: Preparation of γ-Hydroxy-α-L-amino Acids.
✍ Scribed by T. MIURA; N. MASUO; Y. FUSAMAE; T. KAJIMOTO; Y. IDA
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 31 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Kynureninase in Organic Synthesis: Preparation of γ-Hydroxy-α-Lamino Acids.
-Kynureninase catalyzes the transaldol reaction between aromatic and propargylic aldehydes and kynurenine (I). The configuration of the newly formed chiral center at the γ-position of the major isomers (III) is determined to be R.
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Facile Stereoselective Synthesis of γ-Substituted γ-Amino Acids from the Corresponding α-Amino Acids. -The mild and short procedure presented is compatible with common side-chain protecting groups, sensitive functionalities and preserves the chirality of the starting α-amino acid.