Asymmetric Hydrogenation of Cyclic Dipeptides Containing α,β-Dehydroamino Acid Residues and Subsequent Preparation of Optically Pure α-Amino Acids

ABSTRACT Alcaligenes denitrificans Y2k-2 was obtained by selective enrichment followed by screening from soil samples, which showed ω-amino acid:pyruvate transaminase activity, to kinetically resolve aliphatic β-amino acid, and the corresponding structural gene (aptA) was cloned. The gene was functionally expressed in Escherichia coli BL21 by using an isopropyl-β-d-thiogalactopyranoside (IPTG)-inducible pET expression system (9.6 U/mg), and the recombinant AptA was purified to show a specific activity of 77.2 U/mg for l-β-amino-n-butyric acid (l-β-ABA). The enzyme converts various β-amino acids and amines to the corresponding β-keto acids and ketones by using pyruvate as an amine acceptor. The apparent Km and V max for l-β-ABA were 56 mM and 500 U/mg, respectively, in the presence of 10 mM pyruvate. In the presence of 10 mM l-β-ABA, the apparent Km and V max for pyruvate were 11 mM and 370 U/mg, respectively. The enzyme exhibits high stereoselectivity (E > 80) in the kinetic resolution of 50 mM d,l-β-ABA, producing optically pure d-β-ABA (99% enantiomeric excess) with 53% conversion.

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Ti-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino Acids

Journal of the American Chemical Society ◽

10.1021/ja9840605 ◽

1999 ◽

Vol 121 (17) ◽

pp. 4284-4285 ◽

Cited By ~ 166

Author(s):

Clinton A. Krueger ◽

Kevin W. Kuntz ◽

Carolyn D. Dzierba ◽

Wolfgang G. Wirschun ◽

John D. Gleason ◽

...

Keyword(s):

Amino Acids ◽

Practical Synthesis ◽

Enantioselective Addition ◽

Optically Pure

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Asymmetric Hydrogenation of Cyclic Dipeptides Containing α,β-Dehydroamino Acid Residues and Subsequent Preparation of Optically Pure α-Amino Acids

ChemInform Abstract: ASYMMETRIC HYDROGENATION OF α,β-DEHYDROAMINO ACID RESIDUE IN CYCLIC DIPEPTIDES

ChemInform Abstract: EFFICIENT ASYMMETRIC SYNTHESIS OF α-AMINO ACIDS THROUGH HYDROGENATION OF α,β-DEHYDROAMINO ACID RESIDUE IN CYCLIC DIPEPTIDES

Efficient asymmetric synthesis of α-amino acids through hydrogenation of α,β-dehydroamino acid residue in cyclic dipeptides

Unusual amino acids VI. Substituted arylamino acids by asymmetric hydrogenation ofN-Cbz andN-Boc protected dehydroamino acid derivatives

Asymmetric hydrogenation of .alpha.,.beta.-dehydroamino acid residue in cyclic dipeptides

ChemInform Abstract: Asymmetric Synthesis of Unusual Amino Acids: Synthesis of the Optically Pure Isomers of Indole-Protected β-Methyltryptophan Suitable for Peptide Synthesis.

Hydantoinase from Agrobacterium tumefaciens and its use for the preparation of optically pure N-carbamyl-D-amino acids from racemic hydantoins

Free Radical-Mediated Tandem Reaction of Dehydroamino Acid Derivative with π-Allyl Palladium Complex: Synthesis of α,α-Disubstituted Amino Acids

ω-Amino Acid:Pyruvate Transaminase from Alcaligenes denitrificans Y2k-2: a New Catalyst for Kinetic Resolution of β-Amino Acids and Amines

Ti-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino Acids

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