A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols

A new racemic naphthyl‐coumarin‐based probe was found to bind covalently with amino acids in MeOH‐KOH system and thereby generates distinct CD responses. The induced strong CD signals allowed quantitative enantiomeric excess analysis of amino acids and enantioselective sensing of amines and amino al...

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Published in:ChemistryOpen (Weinheim) 2022-06, Vol.11 (6), p.e202200088-n/a
Main Authors: Li, Jia‐Yi, Wang, Li, Yin, Li‐Ping, Jiang, Xin‐Meng, Guo, Kai, Zhang, Chun, Yu, Shan‐Shan, Yu, Xiao‐Qi, Wang, Qin
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Aldehydes
Amines
Amines - chemistry
Amino acids
Amino Acids - chemistry
Amino Alcohols - chemistry
chiral amine
circular dichroism
Coumarin
Coumarins
Enantiomers
enantioselective recognition
naphthyl-coumarin
NMR
Nuclear magnetic resonance
racemic probe
Stereoisomerism
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Summary:A new racemic naphthyl‐coumarin‐based probe was found to bind covalently with amino acids in MeOH‐KOH system and thereby generates distinct CD responses. The induced strong CD signals allowed quantitative enantiomeric excess analysis of amino acids and enantioselective sensing of amines and amino alcohols. The mechanism for the reaction of the coumarin‐aldehyde probe with an amino acid was investigated by CD, UV‐Vis, NMR, ESI‐MS analyses and ECD calculation. A racemic naphthyl‐coumarin‐based probe is developed to covalently bind with amino acids, amines and amino alcohols and thereby generating distinct circular dichroism (CD) signals that allow for the quantitative analysis of the enantiomeric excess and assignment of the absolute configuration for amino acids and enantioselective sensing of amines and amino alcohols.
ISSN:2191-1363
2191-1363
DOI:10.1002/open.202200088