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Solution‐phase synthesis and evaluation of tetraproline chiral stationary phases
Author(s) -
Dai Zhi,
Ye Guozhong,
Pittman Charles U.,
Li Tingyu
Publication year - 2012
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.22001
Subject(s) - chemistry , chiral stationary phase , combinatorial chemistry , chirality (physics) , solid phase synthesis , phase (matter) , chromatography , peptide synthesis , analyte , stationary phase , homogeneity (statistics) , amino acid , organic chemistry , peptide , biochemistry , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model , statistics , mathematics
A protocol was developed for the solution‐phase synthesis of multigram amounts of two 9‐fluorenylmethoxycarbonyl (Fmoc)‐protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution‐phase‐synthesized tetraproline CSPs with that prepared by stepwise solid‐phase synthesis revealed that all three had similar chromatographic performance for resolving 53 model analytes. This suggests that the solution‐phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid‐phase synthesis of oligoproline CSPs. Chirality, 2012. © 2012 Wiley Periodicals, Inc.