A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols
Abstract 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...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2022-06-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202200088 |
| _version_ | 1811344382714970112 |
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| author | Jia‐Yi Li Dr. Li Wang Li‐Ping Yin Xin‐Meng Jiang Dr. Kai Guo Dr. Chun Zhang Dr. Shan‐Shan Yu Prof. Dr. Xiao‐Qi Yu Prof. Dr. Qin Wang |
| author_facet | Jia‐Yi Li Dr. Li Wang Li‐Ping Yin Xin‐Meng Jiang Dr. Kai Guo Dr. Chun Zhang Dr. Shan‐Shan Yu Prof. Dr. Xiao‐Qi Yu Prof. Dr. Qin Wang |
| author_sort | Jia‐Yi Li |
| collection | DOAJ |
| description | Abstract 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. |
| first_indexed | 2024-04-13T19:46:28Z |
| format | Article |
| id | doaj.art-8c51040bc0244e4e9237fa6459b8fc65 |
| institution | Directory Open Access Journal |
| issn | 2191-1363 |
| language | English |
| last_indexed | 2024-04-13T19:46:28Z |
| publishDate | 2022-06-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj.art-8c51040bc0244e4e9237fa6459b8fc652022-12-22T02:32:42ZengWiley-VCHChemistryOpen2191-13632022-06-01116n/an/a10.1002/open.202200088A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino AlcoholsJia‐Yi Li0Dr. Li Wang1Li‐Ping Yin2Xin‐Meng Jiang3Dr. Kai Guo4Dr. Chun Zhang5Dr. Shan‐Shan Yu6Prof. Dr. Xiao‐Qi Yu7Prof. Dr. Qin Wang8Department of Medicinal Chemistry School of Pharmacy Southwest Medical University Luzhou Sichuan 646000 P. R.ChinaNuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province Luzhou Sichuan 646099 P. R. ChinaDepartment of Medicinal Chemistry School of Pharmacy Southwest Medical University Luzhou Sichuan 646000 P. R.ChinaDepartment of Medicinal Chemistry School of Pharmacy Southwest Medical University Luzhou Sichuan 646000 P. R.ChinaDepartment of Medicinal Chemistry School of Pharmacy Southwest Medical University Luzhou Sichuan 646000 P. R.ChinaDepartment of Medicinal Chemistry School of Pharmacy Southwest Medical University Luzhou Sichuan 646000 P. R.ChinaKey Laboratory of Green Chemistry and Technology Ministry of Education College of Chemistry Sichuan University Chengdu Sichuan 610064 P. R. ChinaKey Laboratory of Green Chemistry and Technology Ministry of Education College of Chemistry Sichuan University Chengdu Sichuan 610064 P. R. ChinaDepartment of Medicinal Chemistry School of Pharmacy Southwest Medical University Luzhou Sichuan 646000 P. R.ChinaAbstract 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.https://doi.org/10.1002/open.202200088chiral aminecircular dichroismenantioselective recognitionnaphthyl-coumarinracemic probe |
| spellingShingle | Jia‐Yi Li Dr. Li Wang Li‐Ping Yin Xin‐Meng Jiang Dr. Kai Guo Dr. Chun Zhang Dr. Shan‐Shan Yu Prof. Dr. Xiao‐Qi Yu Prof. Dr. Qin Wang A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols ChemistryOpen chiral amine circular dichroism enantioselective recognition naphthyl-coumarin racemic probe |
| title | A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols |
| title_full | A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols |
| title_fullStr | A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols |
| title_full_unstemmed | A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols |
| title_short | A Racemic Naphthyl‐Coumarin‐Based Probe for Quantitative Enantiomeric Excess Analysis of Amino Acids and Enantioselective Sensing of Amines and Amino Alcohols |
| title_sort | racemic naphthyl coumarin based probe for quantitative enantiomeric excess analysis of amino acids and enantioselective sensing of amines and amino alcohols |
| topic | chiral amine circular dichroism enantioselective recognition naphthyl-coumarin racemic probe |
| url | https://doi.org/10.1002/open.202200088 |
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