Synthesis of novel chiral polyamide macrocycles containing pyridyl side-arms and their molecular recognition properties

Xiao Chen; Da Ming Du; Wen Ting Hua

doi:10.1016/S0957-4166(03)00173-3

Synthesis of novel chiral polyamide macrocycles containing pyridyl side-arms and their molecular recognition properties

Xiao Chen, Da Ming Du, Wen Ting Hua^*

^*Corresponding author for this work

Peking University

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

Seven novel C₂-symmetrical macrocycles containing pyridyl units have been prepared by the cyclic condensation of homochiral diamide intermediates with 2,6-pyridinedicarbonyl dichloride under high dilution at room temperature. The molecular recognition of these homochiral macrocycles for amino acid derivatives has been characterized by various spectroscopic methods such as IR, FAB-MS, fluorescence and UV-vis. The macrocycle 11 exhibited significant chiral recognition towards the enantiomers of D- and L-alanine methyl ester hydrochlorides for which association constants have been determined. Molecular modeling was also used to simulate the interaction mode between the hosts and the guests.

Original language	English
Pages (from-to)	999-1007
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	14
Issue number	8
DOIs	https://doi.org/10.1016/S0957-4166(03)00173-3
Publication status	Published - 18 Apr 2003
Externally published	Yes

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title = "Synthesis of novel chiral polyamide macrocycles containing pyridyl side-arms and their molecular recognition properties",

abstract = "Seven novel C2-symmetrical macrocycles containing pyridyl units have been prepared by the cyclic condensation of homochiral diamide intermediates with 2,6-pyridinedicarbonyl dichloride under high dilution at room temperature. The molecular recognition of these homochiral macrocycles for amino acid derivatives has been characterized by various spectroscopic methods such as IR, FAB-MS, fluorescence and UV-vis. The macrocycle 11 exhibited significant chiral recognition towards the enantiomers of D- and L-alanine methyl ester hydrochlorides for which association constants have been determined. Molecular modeling was also used to simulate the interaction mode between the hosts and the guests.",

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AU - Chen, Xiao

AU - Du, Da Ming

AU - Hua, Wen Ting

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N2 - Seven novel C2-symmetrical macrocycles containing pyridyl units have been prepared by the cyclic condensation of homochiral diamide intermediates with 2,6-pyridinedicarbonyl dichloride under high dilution at room temperature. The molecular recognition of these homochiral macrocycles for amino acid derivatives has been characterized by various spectroscopic methods such as IR, FAB-MS, fluorescence and UV-vis. The macrocycle 11 exhibited significant chiral recognition towards the enantiomers of D- and L-alanine methyl ester hydrochlorides for which association constants have been determined. Molecular modeling was also used to simulate the interaction mode between the hosts and the guests.

AB - Seven novel C2-symmetrical macrocycles containing pyridyl units have been prepared by the cyclic condensation of homochiral diamide intermediates with 2,6-pyridinedicarbonyl dichloride under high dilution at room temperature. The molecular recognition of these homochiral macrocycles for amino acid derivatives has been characterized by various spectroscopic methods such as IR, FAB-MS, fluorescence and UV-vis. The macrocycle 11 exhibited significant chiral recognition towards the enantiomers of D- and L-alanine methyl ester hydrochlorides for which association constants have been determined. Molecular modeling was also used to simulate the interaction mode between the hosts and the guests.

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U2 - 10.1016/S0957-4166(03)00173-3

DO - 10.1016/S0957-4166(03)00173-3

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 8

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Synthesis of novel chiral polyamide macrocycles containing pyridyl side-arms and their molecular recognition properties

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