Chemical Kinetic Resolution of Unprotected β-Substituted β-Amino Acids Using Recyclable Chiral Ligands

2014 ◽  
Vol 126 (30) ◽  
pp. 8017-8020 ◽  
Author(s):  
Shengbin Zhou ◽  
Jiang Wang ◽  
Xia Chen ◽  
José Luis Aceña ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Chemical Kinetic ◽  
Chiral Ligands

Chemical Kinetic Resolution of Unprotected β-Substituted β-Amino Acids Using Recyclable Chiral Ligands

2014 ◽  
Vol 53 (30) ◽  
pp. 7883-7886 ◽  
Author(s):  
Shengbin Zhou ◽  
Jiang Wang ◽  
Xia Chen ◽  
José Luis Aceña ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Chemical Kinetic ◽  
Chiral Ligands

Comparative study of different chiral ligands for dynamic kinetic resolution of amino acids

Chirality ◽  
2021 ◽  
Vol 33 (10) ◽  
pp. 685-702
Author(s):  
Keita Nagaoka ◽  
Arina Nakano ◽  
Jianlin Han ◽  
Tsubasa Sakamoto ◽  
Hiroyuki Konno ◽  
...  
Keyword(s):  
Amino Acids ◽  
Comparative Study ◽  
Kinetic Resolution ◽  
Chiral Ligands ◽  
Dynamic Kinetic Resolution

scholarly journals Recyclable and Stable α-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free C,N-Unprotected α-Amino Acids

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2218
Author(s):  
Shuangjie Shu ◽  
Liang Zhao ◽  
Shengbin Zhou ◽  
Chenglin Wu ◽  
Hong Liu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Kinetic Resolution ◽  
Chiral Ligands ◽  
Chiral Ligand ◽  
Quaternary Carbon ◽  
Dynamic Kinetic Resolution ◽  
High Yields

A novel special designed, stable, and recyclable chiral ligand bearing a quaternary carbon was developed for chemical dynamic kinetic resolution (DKR) of free C,N-unprotected racemic α-amino acids via Schiff base intermediates. This method furnishes high yields with excellent enantioselectivity, has a broad substrate scope, and uses operationally simple and convenient conditions. The present chemical DKR is a practical and useful method for the preparation of enantiopure α-amino acids.

Stereoselective Synthesis ofanti-β-Hydroxy-α-amino Acids through Dynamic Kinetic Resolution

2004 ◽  
Vol 116 (7) ◽  
pp. 900-902 ◽  
Author(s):  
Kazuishi Makino ◽  
Takayuki Goto ◽  
Yasuhiro Hiroki ◽  
Yasumasa Hamada
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Dynamic Kinetic Resolution

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

2004 ◽  
Vol 70 (4) ◽  
pp. 2529-2534 ◽  
Author(s):  
Hyungdon Yun ◽  
Seongyop Lim ◽  
Byung-Kwan Cho ◽  
Byung-Gee Kim
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Specific Activity ◽  
Expression System ◽  
Enantiomeric Excess ◽  
Selective Enrichment ◽  
Alcaligenes Denitrificans ◽  
Keto Acids ◽  
Optically Pure ◽  
High Stereoselectivity

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.

Recyclable Ligands for the Non-Enzymatic Dynamic Kinetic Resolution of Challenging α-Amino Acids

2015 ◽  
Vol 54 (44) ◽  
pp. 12918-12922 ◽  
Author(s):  
Yong Nian ◽  
Jiang Wang ◽  
Shengbin Zhou ◽  
Shuni Wang ◽  
Hiroki Moriwaki ◽  
...  
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution

Enzymatic Dynamic Kinetic Resolution of Oxazinones: A New Approach to Enantiopure β2-Amino Acids

ChemCatChem ◽  
2011 ◽  
Vol 3 (2) ◽  
pp. 319-330 ◽  
Author(s):  
Albrecht Berkessel ◽  
Ilona Jurkiewicz ◽  
Resmi Mohan
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
New Approach

Kinetic Resolution ofd,l-Amino Acids Based on Gas-Phase Dissociation of Copper(II) Complexes

1999 ◽  
Vol 71 (19) ◽  
pp. 4427-4429 ◽  
Author(s):  
W. Andy Tao ◽  
Duxi Zhang ◽  
Feng Wang ◽  
Peter D. Thomas ◽  
R. Graham Cooks
Keyword(s):  
Amino Acids ◽  
Gas Phase ◽  
Kinetic Resolution ◽  
Gas Phase Dissociation
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