Formation of Optically Pure Cyclic Amines by Intramolecular Conjugate Displacement

2012 ◽  
Vol 77 (7) ◽  
pp. 3348-3364 ◽  
Author(s):  
Ping Cheng ◽  
Derrick L. J. Clive
Keyword(s):  
Cyclic Amines ◽  
Intramolecular Conjugate Displacement ◽  
Optically Pure

Efficient Preparation of Optically Pure C2-Symmetrical Cyclic Amines for Chiral Auxiliary.

ChemInform ◽  
2004 ◽  
Vol 35 (43) ◽  
Author(s):  
Mitsuo Sato ◽  
Yasuhiko Gunji ◽  
Taketo Ikeno ◽  
Tohru Yamada
Keyword(s):  
Chiral Auxiliary ◽  
Cyclic Amines ◽  
Optically Pure

A Peptoid with Extended Shape in Water

2019 ◽  
Author(s):  
Jumpei Morimoto ◽  
Yasuhiro Fukuda ◽  
Takumu Watanabe ◽  
Daisuke Kuroda ◽  
Kouhei Tsumoto ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Dimensional Space ◽  
Three Dimensional ◽  
Biomolecular Recognition ◽  
Biological Application ◽  
New Class ◽  
Proteolytic Resistance ◽  
Pharmacokinetic Properties ◽  
Optically Pure ◽  
Three Dimensional Space

<div> <div> <div> <p>“Peptoids” was proposed, over decades ago, as a term describing analogs of peptides that exhibit better physicochemical and pharmacokinetic properties than peptides. Oligo-(N-substituted glycines) (oligo-NSG) was previously proposed as a peptoid due to its high proteolytic resistance and membrane permeability. However, oligo-NSG is conformationally flexible and is difficult to achieve a defined shape in water. This conformational flexibility is severely limiting biological application of oligo-NSG. Here, we propose oligo-(N-substituted alanines) (oligo-NSA) as a new peptoid that forms a defined shape in water. A synthetic method established in this study enabled the first isolation and conformational study of optically pure oligo-NSA. Computational simulations, crystallographic studies and spectroscopic analysis demonstrated the well-defined extended shape of oligo-NSA realized by backbone steric effects. The new class of peptoid achieves the constrained conformation without any assistance of N-substituents and serves as an ideal scaffold for displaying functional groups in well-defined three-dimensional space, which leads to effective biomolecular recognition. </p> </div> </div> </div>

Flavin/I2 -Catalyzed Aerobic Oxidative C-H Sulfenylation of Aryl-Fused Cyclic Amines

2020 ◽  
Vol 2020 (25) ◽  
pp. 3889-3895 ◽  
Author(s):  
Xinpeng Jiang ◽  
Zongchen Zhao ◽  
Zhifeng Shen ◽  
Keda Chen ◽  
Liyun Fang ◽  
...  
Keyword(s):  
Cyclic Amines

Copper(II) mediated C-8 amination of 1-naphthylamide derivatives with acyclic and cyclic amines

2021 ◽  
pp. 152858
Author(s):  
Tapan Sahoo ◽  
Souvik Sarkar ◽  
Subhash Chandra Ghosh
Keyword(s):  
Cyclic Amines

scholarly journals Altering the Stereoselectivity of Whole-Cell Biotransformations via the Physicochemical Parameters Impacting the Processes

Catalysts ◽  
2021 ◽  
Vol 11 (7) ◽  
pp. 781
Author(s):  
Agnieszka Raczyńska ◽  
Joanna Jadczyk ◽  
Małgorzata Brzezińska-Rodak
Keyword(s):  
Culture Conditions ◽  
Biologically Active ◽  
Enantiomerically Pure ◽  
Whole Cells ◽  
Chiral Compounds ◽  
Physicochemical Factors ◽  
Pure Compounds ◽  
Genetic Level ◽  
Prochiral Ketones ◽  
Optically Pure

The enantioselective synthesis of organic compounds is one of the great challenges in organic synthetic chemistry due to its importance for the acquisition of biologically active derivatives, e.g., pharmaceuticals, agrochemicals, and others. This is why biological systems are increasingly applied as tools for chiral compounds synthesis or modification. The use of whole cells of “wild-type” microorganisms is one possible approach, especially as some methods allow improving the conversion degrees and controlling the stereoselectivity of the reaction without the need to introduce changes at the genetic level. Simple manipulation of the culture conditions, the form of a biocatalyst, or the appropriate composition of the biotransformation medium makes it possible to obtain optically pure products in a cheap, safe, and environmentally friendly manner. This review contains selected examples of the influence of physicochemical factors on the stereochemistry of the biocatalytic preparation of enantiomerically pure compounds, which is undertaken through kinetically controlled separation of their racemic mixtures or reduction of prochiral ketones and has an effect on the final enantiomeric purity and enantioselectivity of the reaction.

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