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Abstract Three BINOL‐based unsymmetric chiral dialdehydes, (S)‐4, (S)‐5, and (S)‐6, each containing a salicylaldehyde moiety and anortho‐,meta‐ orpara‐substituted benzaldehyde unit, are synthesized and used to react with the enantiomers of an unsymmetric chiral diamine, lysine. These reactions represent the first examples of regioselective as well as enantioselective reactions of an unsymmetric chiral dialdehyde with an unsymmetric chiral diamine to generate unsymmetric chiral macrocycles. The addition of Zn2+can further enhance the selectivity for the macrocycle formation. Compounds (S)‐4and (S)‐5are found to exhibit chemoselective and enantioselective fluorescent recognition of lysine in the presence of Zn2+.
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Near‐IR Fluorescent Recognition of Arginine: High Chemoselectivity and Enantioselectivity Promoted by La 3+
Abstract The first near IR fluorescent probe for the chemoselective and enantioselective recognition of arginine in aqueous solution is reported in this work. This probe, made of a 1,1’‐binaphthyl‐based chiral aldehyde unit and a rhodamine‐based near IR chromophore, in combination with La3+exhibits highly chemoselective as well as enantioselective fluorescent enhancement with arginine at λ=764 nm upon excitation at λ=690 nm. Little or no fluorescent response is observed toward the chirality miss‐matched arginine enantiomer or other common amino acids and their enantiomers. This probe also allows visual discrimination of the arginine enantiomers because of its fast and distinct color change upon interaction with the substrate.
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- Award ID(s):
- 2153466
- PAR ID:
- 10418468
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- ChemPlusChem
- Volume:
- 88
- Issue:
- 6
- ISSN:
- 2192-6506
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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