Premium
Immobilization of difunctional building blocks on hydroxysuccinimide activated silica: Versatile in situ preparation of chiral stationary phases
Author(s) -
Kosjek Birgit,
Uray Georg
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10020
Subject(s) - chemistry , enantiomer , diamine , amino acid , organic chemistry , combinatorial chemistry , biochemistry
Several brush‐type chiral stationary phases (CSPs) based on undecanoyl‐ or butanoyl‐bound (R,R)‐1,2‐diphenylethane‐1,2‐diamine (DPEDA) as chiral selector were prepared by an innovative, fast, and less expensive kind of preparation. The key to this method is the immobilization of the enantiomeric pure diamine with only one amino function in a simple substitution reaction on hydroxysuccinimide ester‐activated silica. No excess chiral material is lost. Loading can be easily monitored analyzing the filtrate. The free second amino function can subsequently be acylated with different acyl halogenides. Examples with benzoyl‐ and 3,5‐dinitrobenzoyl (DNB) amides show that, based on our new approach, a library of differently acylated Pirkle‐type CSPs can easily be obtained. A benzoylated analog of the commercially available ULMO CSP is shown to be very effective in separating enantiomers of N‐acyl amino acids. Chirality 13:657–667, 2001. © 2001 Wiley‐Liss, Inc.