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Lanthanide Tris(β‐diketonates) as Useful Probes for Chirality Determination of Biological Amino Alcohols in Vibrational Circular Dichroism: Ligand to Ligand Chirality Transfer in Lanthanide Coordination Sphere
Author(s) -
Miyake Hiroyuki,
Terada Keiko,
Tsukube Hiroshi
Publication year - 2014
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.22319
Subject(s) - chemistry , chirality (physics) , lanthanide , vibrational circular dichroism , circular dichroism , ligand (biochemistry) , enantiomer , axial chirality , stereochemistry , coordination complex , crystallography , photochemistry , enantioselective synthesis , organic chemistry , catalysis , metal , ion , biochemistry , physics , chiral symmetry breaking , receptor , quantum mechanics , nambu–jona lasinio model , quark
A series of lanthanide tris(β‐diketonates) functioned as useful chirality probes in the vibrational circular dichroism (VCD) characterization of biological amino alcohols. Various chiral amino alcohols induced intense VCD signals upon ternary complexation with racemic lanthanide tris(β‐diketonates). The VCD signals observed around 1500 cm −1 (β‐diketonate IR absorption region) correlated well with the stereochemistry and enantiomeric purity of the targeted amino alcohol, while the corresponding monoalcohol, monoamine, and diol substrates induced very weak VCD signals. The high‐coordination number and dynamic property of the lanthanide complex offer an effective chirality VCD probing of biological substrates. Chirality 26:293–299, 2014 . © 2014 Wiley Periodicals, Inc.