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Enantioselective Discrimination of Histidine by Means of an Achiral Cubane-Bridged Bis-Porphyrin.

ABSTRACT: A Langmuir film of cubane-bridged bisporphyrin (H₂por-cubane-H₂por) at the air/water interface was developed and characterized. The floating film was successfully employed for the chiral discrimination between l- and d-histidine. The enantioselective behavior persisted after the deposition of the film on a solid support using the Langmuir-Schaefer method. Distinct absorption and reflection spectra were observed in the presence of l- or d-histidine, revealing that conformational switching was governed by the interaction between H₂por-cubane-H₂por and the histidine enantiomer. The mechanism of chiral selection was investigated using an ad hoc modified nulling ellipsometer, indicating the anti-conformation was dominant in the presence of l-histidine, whereas the presence of d-histidine promoted the formation of tweezer conformation.

SUBMITTER: Bettini S

PROVIDER: S-EPMC8638291 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Enantioselective Discrimination of Histidine by Means of an Achiral Cubane-Bridged Bis-Porphyrin.

Bettini Simona S Grover Nitika N Ottolini Michela M Mattern Cornelia C Valli Ludovico L Senge Mathias O MO Giancane Gabriele G

Langmuir : the ACS journal of surfaces and colloids 20211116 47

A Langmuir film of cubane-bridged bisporphyrin (H2por-cubane-H2por) at the air/water interface was developed and characterized. The floating film was successfully employed for the chiral discrimination between l- and d-histidine. The enantioselective behavior persisted after the deposition of the film on a solid support using the Langmuir-Schaefer method. Distinct absorption and reflection spectra were observed in the presence of l- or d-h ...[more]

PMID: 34784714

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