- Synthesis of γ-halogenated and long-chain β-hydroxy-α-amino acids and 2-amino-1,3-diols using threonine aldolases
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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.
- Steinreiber, Johannes,Fesko, Kateryna,Mayer, Clemens,Reisinger, Christoph,Schürmann, Martin,Griengl, Herfried
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p. 8088 - 8093
(2008/02/08)
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- L-threonine aldolase in organic synthesis: Preparation of novel β-hydroxy-α-amino acids
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The L-threonine aldolase from Candida humicola was used in the synthesis of multifunctional β-hydroxy-α-amino acids. Of many aldehydes with different substituents tested as substrates for reaction with glycine, benzyloxy- and alkoxy-aldehydes are found to be good substrates, providing a new synthetic route to α-amino-β,ω-dihydroxy and α,ω-diamino-β-hydroxy acids. The enzymatic reactions are not stereospecific regarding the new stereocenter formed at the β-carbon, though they all give L-α-amino acids.
- Kajimoto, Tetsuya
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p. 4081 - 4084
(2007/10/02)
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- Structure and Stereochemistry of Three Phytotoxins, Syringomycin, Syringotoxin and Syringostatin, Produced by Pseudomonas syringae pv. syringae
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The structures of two phytotoxins, syringomycin and syringotoxin, produced by Pseudomonas syringae pv. syringae, were determined.Several amino acid residues of syringomycin were different from those in the syringostatins.Syringotoxin B proved to be syringostatin A.The three kinds of phytotoxins showed close structural similarity, and the stereochemistry of their components was deduced and compared.
- Fukuchi, Naoyuka,Isogai, Akira,Nakayama, Jiro,Takayama, Seiji,Yamashita, Shuichi,et al.
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p. 1149 - 1158
(2007/10/02)
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- 2-oxoazetidin-1-yloxy acetic acids and analogs
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Antibiotic activity is exhibited by β-lactams having an STR1 substituent (and analogs thereof) in the 1-position and an acylamino substituent in the 3-position.
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