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Enantioselective Recognition of Aspartic Acids by Chiral Ligand Exchange Potentiometry
Author(s) -
Zhou Yanxiu,
Yu Bin,
Levon Kalle,
Nagaoka Tsutomu
Publication year - 2004
Publication title -
electroanalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 128
eISSN - 1521-4109
pISSN - 1040-0397
DOI - 10.1002/elan.200302904
Subject(s) - enantioselective synthesis , chemistry , enantiomer , ligand (biochemistry) , aspartic acid , stereochemistry , stereoselectivity , chirality (physics) , medicinal chemistry , catalysis , combinatorial chemistry , amino acid , organic chemistry , receptor , biochemistry , physics , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics , quark
Enantioselective resolution is realized by combining potentiometry with ligand exchange (CE) in a new method called chiral ligand exchange potentiometry (CLEP). A chiral selector, N ‐carbobenzoxy‐ L ‐aspartic acid (N‐CBZ‐L‐Asp), preferentially recognizes D ‐aspartic acid (D‐Asp) and undergoes ligand exchange with the enantiomeric labile coordination complexes of [Cu(II)(D‐Asp) 2 ] or [Cu(II)(L‐Asp) 2 ] to form a diastereoisomeric complex [(D‐Asp)Cu(II)(N‐CBZ‐L‐Asp)] (a) or [(L‐Asp)Cu(II)(N‐CBZ‐L‐Asp)] (b). Considerable stereoselectivity occurs in the formation of these diastereoisomeric complexes, and their net charges were −2 (a) and 0 (b), respectively, resulting in different Nernst factor (electrode slope), thus enabling chiral D‐Asp to be distinguished by potentiometry without any pre‐ or postseparation processes.