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Enantiomeric separation of amino alcohols using Z‐L‐glu‐L‐pro or Z‐L‐glu‐D‐pro as chiral counter ions and hypercarb as the solid phase
Author(s) -
Karlsson Anders,
Karlsson Olle
Publication year - 1997
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/(sici)1520-636x(1997)9:7<650::aid-chir2>3.0.co;2-b
Subject(s) - chemistry , enantiomer , enantioselective synthesis , chirality (physics) , diastereomer , amino acid , chiral derivatizing agent , enantiomeric excess , chiral auxiliary , solvent , stereochemistry , ion , methanol , chiral resolution , medicinal chemistry , chiral column chromatography , organic chemistry , catalysis , physics , quantum mechanics , nambu–jona lasinio model , quark , biochemistry , chiral symmetry breaking
This paper describes the synthesis of two new N‐derivatized dipeptides. The two compounds, N‐benzyloxycarbonyl‐L‐glutamyl‐L‐proline (Z‐L‐glu‐L‐pro) and N‐benzyloxycarbonyl‐L‐glutamyl‐D‐proline (Z‐L‐glu‐D‐pro), were tested as chiral counter ions for the enantiomeric resolution of amino alcohols. The chiral counter ions were dissolved in a polar solvent, e.g., methanol and porous graphitic carbon, Hypercarb, were used as the achiral solid phase. The enantiomers of several of the tested compounds were baseline separated using Z‐L‐glu‐L‐pro as the chiral counter ion but no enantioselective retention was obtained using its diastereoisomer Z‐L‐glu‐D‐pro. The influence of solute structure as well as the importance of converting the chiral counter ion to its dianionic form will be described together with the effect of column temperature on enantioselective retention. Chirality 9:650–655, 1997. © 1997 Wiley‐Liss, Inc.