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Reactions of Unsymmetric Chiral Dialdehydes with Lysine: Regio‐ and Enantioselective Macrocyclization and Fluorescent Sensing

https://doi.org/10.1002/ejoc.202401250

Mao, Yifan; Li, Yichen; Davis, Stephanie; Pu, Lin (January 2025, European Journal of Organic Chemistry)

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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Regio- and Enantioselective Macrocyclization from Dynamic Imine Formation: Chemo- and Enantioselective Fluorescent Recognition of Lysine

https://doi.org/10.1021/acs.orglett.3c02949

Mao, Yifan; Davis, Stephanie; Pu, Lin (October 2023, Organic Letters)

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One Molecular Probe with Opposite Enantioselective Fluorescence Enhancement at Two Distinct Emissions

https://doi.org/10.1021/acs.orglett.3c00692

Mao, Yifan; Thomae, Evan; Davis, Stephanie; Wang, Chengyang; Li, Yichen; Pu, Lin (March 2023, Organic Letters)

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Determining the concentration and enantiomeric composition of histidine using one fluorescent probe

https://doi.org/10.1039/d0cc07498e

Mao, Yifan; Abed, Mehdi A.; Lee, Nathan B.; Wu, Xuedan; Du, Gengyu; Pu, Lin (January 2021, Chemical Communications)
null (Ed.)
A chemoselective as well as enantioselective fluorescent probe has been developed to determine both the concentration and enantiomeric composition of the biologically important amino acid histidine by measuring the fluorescence responses when excited at two different wavelengths.
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Fluorescent recognition of l - and d -tryptophan in water by micelle probes

https://doi.org/10.1039/d0qm00260g

Du, Gengyu; Mao, Yifan; Abed, Mehdi A.; Pu, Lin (July 2020, Materials Chemistry Frontiers)
null (Ed.)
A series of BINOL-based monoaldehydes have been designed and synthesized as fluorescent probes for l - and d -tryptophan. It is found that in the presence of a diblock copolymer PEG-PLLA, these probes can be encapsulated into micelles which in combination with Zn 2+ have exhibited chemo- and enantioselective fluorescent enhancement with tryptophan in aqueous media.
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