Preparation of Isoquinolinecarboxylic Acid Derivative as Brush-type Chiral Stationary Phase and Its Application in the Enantiomeric Resolutions of Binaphthol Derivatives

Chem. J. Chinese Universities

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Preparation of Isoquinolinecarboxylic Acid Derivative as Brush-type Chiral Stationary Phase and Its Application in the Enantiomeric Resolutions of Binaphthol Derivatives

SONG Rui-Juan^1,2, GUO Ying^1,2, FU Yu^1,2, SHI Hong-Yu^1,2, LONG Yuan-De¹, HUANG Tian-Bao¹

1. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;
2. Graduate School, the Chinese Academy of Sciences, Beijing 100049, China

Received:2006-06-05 Revised:1900-01-01 Online:2007-01-10 Published:2007-01-10
Contact: HUANG Tian-Bao

Abstract

Abstract: A novel chiral stationary phase(CSP) for HPLC was prepared by synthesizing 3,5-dinitrobenzoyl-(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid as chiral selector and bonding it with 3-aminopropylsilane modified silica. The resolutions of 8 enantiomers of binaphthol and its derivatives were achieved by using hexane-ethanol-acetic acid(98:2:0.5, volume ratio) as mobile phase with a column temperature 30 ℃ and detected at ultraviolet 254 nm. The effects of acetic acid and alcohol organic modifiers on retention and resolutions of the analytes were examined. The enantioselectivities α of the analytes on CSP could be improved by adding acetic acid to mobile phase due to masking effect of H⁺ on the residing silanol and amino group.

Key words: Isoquinoline derivative, Chiral stationary phase, Binaphthol derivative, Organic modifier

CLC Number:

O657

TrendMD:

SONG Rui-Juan^1,2, GUO Ying^1,2, FU Yu^1,2, SHI Hong-Yu^1,2, LONG Yuan-De¹, HUANG Tian-Bao¹. Preparation of Isoquinolinecarboxylic Acid Derivative as Brush-type Chiral Stationary Phase and Its Application in the Enantiomeric Resolutions of Binaphthol Derivatives[J]. Chem. J. Chinese Universities, doi: .

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Preparation of Isoquinolinecarboxylic Acid Derivative as Brush-type Chiral Stationary Phase and Its Application in the Enantiomeric Resolutions of Binaphthol Derivatives

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