Stereochemical analysis of chiral amines, diamines, and amino alcohols: Practical chiroptical sensing based on dynamic covalent chemistry

Chirality ◽  
2020 ◽  
Vol 32 (4) ◽  
pp. 457-463
Author(s):  
Diandra S. Hassan ◽  
F. Yushra Thanzeel ◽  
Christian Wolf
Keyword(s):  
Amino Alcohols ◽  
Chiral Amines ◽  
Dynamic Covalent Chemistry ◽  
Stereochemical Analysis

Quantitative chirality sensing of amines and amino alcohols via Schiff base formation with a stereodynamic UV/CD probe

2016 ◽  
Vol 14 (6) ◽  
pp. 1934-1939 ◽  
Author(s):  
Zeus A. De los Santos ◽  
Ransheng Ding ◽  
Christian Wolf
Keyword(s):  
Schiff Base ◽  
Amino Alcohols ◽  
Chiral Amines ◽  
Schiff Base Formation ◽  
Base Formation

A readily available probe is used for quantitative sensing of the concentration and ee of chiral amines and amino alcohols.

In situ approach for testing the enantiopurity of chiral amines and amino alcohols by1H NMR

2014 ◽  
Vol 12 (3) ◽  
pp. 495-502 ◽  
Author(s):  
Sandeep Kumar Mishra ◽  
Sachin R. Chaudhari ◽  
N. Suryaprakash
Keyword(s):  
Amino Alcohols ◽  
Chiral Amines

Development of an engineered thermostable amine dehydrogenase for the synthesis of structurally diverse chiral amines

2020 ◽  
Vol 10 (8) ◽  
pp. 2353-2358 ◽  
Author(s):  
Lei Liu ◽  
Dong-Hao Wang ◽  
Fei-Fei Chen ◽  
Zhi-Jun Zhang ◽  
Qi Chen ◽  
...  
Keyword(s):  
Amino Alcohols ◽  
Chiral Amines ◽  
Amine Dehydrogenase

Structurally diverse chiral amines and amino alcohols were synthesized using an engineered thermostable amine dehydrogenase, demonstrating its extensive synthesis potential.

Formation and Trapping of the Thermodynamically Unfavoured Inverted-Hemicucurbit[6]uril

2019 ◽  
Author(s):  
Elena Prigorchenko ◽  
Sandra Kaabel ◽  
Triin Narva ◽  
Anastassia Baškir ◽  
Maria Fomitšenko ◽  
...  
Keyword(s):  
Complex Formation ◽  
Combinatorial Chemistry ◽  
Trifluoroacetic Acid ◽  
Chloride Anion ◽  
Binding Affinities ◽  
Dynamic Covalent Chemistry ◽  
Reaction Selectivity ◽  
Low Concentration ◽  
Dynamic Combinatorial Chemistry ◽  
First Time

Amplification of a thermodynamically unfavoured macrocyclic product through the directed shift of the equilibrium between dynamic covalent chemistry library members is difficult to achieve. We show for the first time that during condensation of formaldehyde and <i>cis</i>-<i>N,N'</i>-cyclohexa-1,2-diylurea formation of <i>inverted-cis</i>-cyclohexanohemicucurbit[6]uril (<i>i-cis</i>-cycHC[6]) can be induced at the expense of thermodynamically favoured <i>cis</i>-cyclohexanohemicucurbit[6]uril (<i>cis</i>-cycHC[6]). The formation of <i>i-cis-</i>cycHC[6] is enhanced in low concentration of the templating chloride anion and suppressed in excess of this template. We found that reaction selectivity is governed by the solution-based template-aided dynamic combinatorial chemistry and continuous removal of the formed cycHC[6] macrocycles from the equilibrating solution by precipitation. Notably, the <i>i-cis</i>-cycHC[6] was isolated with 33% yield. Different binding affinities of three diastereomeric <i>i-cis</i>-, <i>cis</i>-cycHC[6] and their chiral isomer (<i>R,R</i>)-cycHC[6] for trifluoroacetic acid demonstrate the influence of macrocycle geometry on complex formation.

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