Helical Chirality Induces a Substrate-Selectivity Switch in Carbohydrates Recognitions | Zendy

A.M. Long | Zendy; Olivier Perraud | Zendy; Muriel Albalat | Zendy; Vincent Robert | Zendy; JeanPierre Dutasta | Zendy; Alexandre Martinez | Zendy

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Helical Chirality Induces a Substrate-Selectivity Switch in Carbohydrates Recognitions

Author(s) -

A.M. Long,

Olivier Perraud,

Muriel Albalat,

Vincent Robert,

JeanPierre Dutasta,

Alexandre Martinez

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b00276

Subject(s) - chirality (physics) , enantiomer , chemistry , selectivity , stereochemistry , circular dichroism , absolute configuration , substrate (aquarium) , amine gas treating , mannose , spectroscopy , organic chemistry , chiral symmetry , physics , quantum mechanics , geology , nambu–jona lasinio model , oceanography , quark , catalysis

A new chiral hemicryptophane cage combining an electron-rich cyclotriveratrylene (CTV) unit and polar amine functions has been synthesized. The resolution of the racemic mixture has been performed by chiral HPLC, and the assignment of the absolute configuration of the two enantiomers has been achieved using ECD spectroscopy. In contrast with other hemicryptophane receptors, the two enantiomeric hosts display both remarkable enantioselectivities in the recognition of carbohydrates and good binding constants. Moreover, by switching the chirality of the CTV unit from M to P, a strong preference shift from glucose to mannose derivatives is observed.

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