Premium
The Enantioresolution of n ‐Benzoyl and Its Analogs Derivatized Amino Acids on Cyclodextrin Bonded Chiral Stationary Phases Using a Nonaqueous Acetonitrile‐Based Mobile Phase
Author(s) -
Chen Shushi
Publication year - 1996
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199600008
Subject(s) - chemistry , stereocenter , amino acid , reagent , enantiomer , amine gas treating , combinatorial chemistry , acetonitrile , cyclodextrin , side chain , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry , polymer
The separation of amino acids into enantiomers while derivatizing with benzoyl chlorides is demonstrated. It was found that enantioselectivity among these reagents tagging with the same amino acid is quite different and is very sensitive to its structural variations. A noninclusion complexation mechanism i.e . external association is thought to involve in the separation carried out with a nonaqueous polar organic mobile phase. Results also indicate that the chiral recognition seems to be controlled either by moieties from tagging reagents or functional groups on all amino acids examined in this study on the basis of competition. The polarity of side‐chain group on peptide backbone can not be ignored in achieving a successful separation. Furthermore, chiral recognition appears to closely rely upon the location of stereogenic center that is simultaneously attached by amino and carboxyl groups. Finally, mechanism involved will be explored structurally with these tagging reagents derivatized amino acids which structures are highly ordered and amine‐containing compounds with structures similar to that of amino acid.