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Fluorous Substituent‐Based Enantiomer and Diastereomer Separation: Orthogonal Use of HPLC Columns for the Synthesis of Nonproteinogenic Polyfluoro Amino Acids and Peptides
Author(s) -
Tonoi Takayuki,
Nishikawa Aya,
Yajima Tomoko,
Nagano Hajime,
Mikami Koichi
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701052
Subject(s) - chemistry , diastereomer , enantiomer , substituent , dipeptide , high performance liquid chromatography , chiral column chromatography , amino acid , organic chemistry , chromatography , stereochemistry , biochemistry
A variety of fluorine‐containing amino acid and dipeptide precursors bearing different lengths of perfluoroalkyl chains were separated into their enantiomers and diastereomers, respectively, by the orthogonal use of fluorous and chiral HPLC columns. These results show the applicability of fluorous racemic mixture synthesis for various “fluorinated” chiral products without introducing conventional cleavable fluorous tags. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)