Bulky melamine-based Zn-porphyrin tweezer as a CD probe of molecular chirality |
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Authors: | Petrovic Ana G Vantomme Ghislaine Negrón-Abril Yashira L Lubian Elisa Saielli Giacomo Menegazzo Ileana Cordero Roselynn Proni Gloria Nakanishi Koji Carofiglio Tommaso Berova Nina |
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Institution: | Department of Life Sciences, New York Institute of Technology (NYIT), New York, New York, USA. |
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Abstract: | The transfer of chirality from a guest molecule to an achiral host is the subject of significant interest especially when, upon chiral induction, the chiroptical response of the host/guest complex can effectively report the absolute configuration (AC) of the guest. For more than a decade, dimeric metalloporphyrin hosts (tweezers) have been successfully applied as chirality probes for determination of the AC for a wide variety of chiral synthetic compounds and natural products. The objective of this study is to investigate the utility of a new class of melamine-bridged Zn-porphyrin tweezers as sensitive AC reporters. A combined approach based on an experimental CD analysis and a theoretical prediction of the prevailing interporphyrin helicity demonstrates that these tweezers display favorable properties for chiral recognition. Herein, we discuss the application of the melamine-bridged tweezer to the chiral recognition of a diverse set of chiral guests, such as 1,2-diamines, α-amino-esters and amides, secondary alcohols, and 1,2-amino-alcohols. The bulky periphery and the presence of a rigid porphyrin linkage lead, in some cases, to a more enhanced CD sensitivity than that reported earlier with other tweezers. |
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