10148-68-2Relevant articles and documents
Synthesis of γ-halogenated and long-chain β-hydroxy-α-amino acids and 2-amino-1,3-diols using threonine aldolases
Steinreiber, Johannes,Fesko, Kateryna,Mayer, Clemens,Reisinger, Christoph,Schürmann, Martin,Griengl, Herfried
, p. 8088 - 8093 (2007)
The l- and d-threonine aldolase catalyzed formation of γ-halogenated and long-chain l- and d-3-alkylserine-derivatives 1-12, respectively, was shown starting from glycine and halogenated C2- or C4-C12 aldehydes. lTA from Pseudomonas putida accepted all tested aldehydes with strongly varying diastereoselectivity (de up to 93%). Only aldehydes smaller than decanal were converted by dTA from Alcaligenes xylosoxidans with good selectivities (de up to 73%). Utilizing isobutanal enantio- and diastereopure d-syn-2-amino-3-hydroxy-4-methylpentanoic acid was obtained (ee>99%, de>95%), which was converted to the corresponding 2-amino-1,3-diol.
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Niimura,Y.,Hatanaka,S.-I.
, p. 175 - 178 (1974)
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ASYMMETRIC ALDOL REACTIONS USING BORON ENOLATES OF CHIRAL OXAZINONES, SYNTHESIS OF L-ALLO-THREONINE
Reno, Daniel S.,Lotz, Bruce T.,Miller, Marvin J.
, p. 827 - 830 (2007/10/02)
The boron enolate of oxazinone 1 was allowed to react with acetaldehyde, butanal, and 2-methylpropanal.The reaction proceeded stereoselectively, and in the reaction with acetaldehyde, the reaction afforded a precursor to L-allo-threonine.