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Gas‐chromatographic separation of stereoisomers of dipeptides
Author(s) -
Pätzold Ralf,
Theis Christoph,
Brückner Hans
Publication year - 2006
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.20290
Subject(s) - chemistry , dipeptide , diastereomer , enantiomer , derivatization , diketopiperazines , chirality (physics) , gas chromatography , chromatography , organic chemistry , peptide , high performance liquid chromatography , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Synthetic dipeptides comprising mixtures of enantiomers, diastereomers, or sequential isomers were converted into their N ‐perfluoroacetyl dipeptide esters (perfluoroacetyl: trifluoroacetyl, pentafluoroacetyl, heptafluorobutyryl; ester: methyl, 1‐propyl, 2‐propyl, 2,2,2‐trifluoroethyl) and analyzed by GC‐MS on the chiral stationary phases Chirasil®‐ L ‐Val and Lipodex®‐ E using helium as carrier gas. Further, dipeptides were converted into their N ‐trifluoroacetyl dipeptide S ‐(+)‐2‐butyl esters and separated on achiral phenylmethyl polysiloxane column (HP‐5 MS). Derivatization of dipeptides was performed at ambient temperature in order to avoid formation of the corresponding diketopiperazines. The best separation of stereoisomers was achieved with TFA and PFP methyl esters on Chirasil®‐ L ‐Val. Chirality 18:551–557, 2006. © 2006 Wiley‐Liss, Inc.