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Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand.

ABSTRACT: We report a chiral deep cavitand receptor based on calix[5]arene stabilized by a cooperative network of hydrogen bonds and having a highly flexible structure. The cavitand displays enantioselective molecular recognition with a series of chiral quaternary ammonium salts, providing unprecedented stability ratios between the corresponding diastereomeric host-guest complexes. Molecular dynamics simulations corroborate the higher flexibility of the new host and the emergence of superior induced-fit behavior with regards to resorcin[4]arene derived self-folding cavitands.

SUBMITTER: Alvarez-Yebra R

PROVIDER: S-EPMC10186369 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

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Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand.

Álvarez-Yebra Rubén R López-Coll Ricard R Galán-Masferrer Pere P Lledó Agustí A

Organic letters 20230411 18

We report a chiral deep cavitand receptor based on calix[5]arene stabilized by a cooperative network of hydrogen bonds and having a highly flexible structure. The cavitand displays enantioselective molecular recognition with a series of chiral quaternary ammonium salts, providing unprecedented stability ratios between the corresponding diastereomeric host-guest complexes. Molecular dynamics simulations corroborate the higher flexibility of the new host and the emergence of superior induced-fit b ...[more]

PMID: 37038894

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