The kinetic resolution of oxazinones by alcoholysis: access to orthogonally protected β-amino acids

2021 ◽  
Author(s):  
Sarah A. Cronin ◽  
Stephen J. Connon
Keyword(s):  
Amino Acids ◽  
Small Molecule ◽  
Kinetic Resolution ◽  
Peptide Chemistry

A small molecule organocatalyst can promote the alcoholytic, highly enantioselective kinetic resolution of 4- and 5-substituted oxazinones to produce orthogonally protected β2- and β3-amino acids ready for use in peptide chemistry.

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

scholarly journals Fluorescent Probes with Unnatural Amino Acids to Monitor Proteasome Activity in Real-Time

2020 ◽  
Author(s):  
Breanna L. Zerfas ◽  
Rachel A. Coleman ◽  
Andres Salazar Chaparro ◽  
Nathaniel J. Macatangay ◽  
Darci Trader
Keyword(s):  
Amino Acids ◽  
Small Molecule ◽  
Fluorescent Probes ◽  
Unnatural Amino Acids ◽  
Cell Types ◽  
Proteasome Activity ◽  
Live Cells ◽  
Fluorescent Substrate ◽  
The Individual ◽  
Small Molecule Modulators

<div> <div> <div> <p>The proteasome is an essential protein complex that, when dysregulated, can result in various diseases in eukaryotic cells. As such, understanding the enzymatic activity of the proteasome and what can alter it is crucial to elucidating its roles in these diseases. This can be done effectively by using activity-based fluorescent substrate probes, of which there are many commercially available that target the individual protease-like subunits in the 20S CP of the proteasome. Unfortunately, these probes have not displayed appropriate characteristics for their use in live cell-based assays. In the work presented here, we have developed a set of probes which have shown improved fluorescence properties and selectivity towards the proteasome compared to other cellular proteases. By including unnatural amino acids, we have found probes which can be utilized in various applications, including monitoring the effects of small molecule stimulators of the proteasome in live cells and comparing the relative proteasome activity across different cancer cell types. In future studies, we expect the fluorescent probes presented here will serve as tools to support the discovery and characterization of small molecule modulators of proteasome activity. </p> </div> </div> </div>

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

2004 ◽  
Vol 43 (7) ◽  
pp. 882-884 ◽  
Author(s):  
Kazuishi Makino ◽  
Takayuki Goto ◽  
Yasuhiro Hiroki ◽  
Yasumasa Hamada
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Dynamic Kinetic Resolution
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