• Title/Summary/Keyword: Chiral discrimination

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The Pfeiffer Effect of [Co$^{II}$(acac)$_2$(diamine)] with Cinchona Alkaloid in Some Organic Solvents

  • Oh, Chang-Eon;Kim, Yang
    • Bulletin of the Korean Chemical Society
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    • v.9 no.6
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    • pp.355-359
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    • 1988
  • The Pfeiffer effect was examined on the systems of racemic [$Co^{II}(acac)_2$(diamine)] with d-cinchonine and l-cinchonidine as chiral environment substances in methanol, ethanol, chloroform and methanol-chloroform mixture solvents. It was found that the ${\Delta}$-enantiomer is enriched for the [$Co^{II}(acac)_2$(diamine)]-d-cinchonine system, but the Λ -enantiomer is enriched for the [$Co^{II}(acac)_2$(diamine)]-l-cinchonidine system. The complexes having no N-H protons such as [$Co^{II}(acac)_2$(bpy)] and [$Co^{II}(acac)_2$(phen)] were Pfeiffer-inactive in alcoholic solvents, where bpy = 2,2'-bipyridine and phen = 1,10-phenanthroline. This was interpreted to mean that the hydrogen bonding between N-H proton of diamine ligand and C-9 hydroxyl group of alkalid plays an important role in the chiral discrimination. And the rate of antiracemization ($k_{anti}$) by the Pfeiffer effect was also measured for the [$Co^{II}(acac)_2$(diamine)]-d-cinchonine system in alcoholic solvents. It was found that the rate of appearance of the Pfeiffer effect was enhanced as the concentration of added chloroform is increased.

Facile Synthesis of the Uryl Pendant Binaphthol Aldehyde and Its Selective Fluorescent Recognition of Tryptophan

  • Tang, Lijun;Wei, Gongfan;Nandhakumar, Raju;Guo, Zhilong
    • Bulletin of the Korean Chemical Society
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    • v.32 no.9
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    • pp.3367-3371
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    • 2011
  • An easy and convenient synthetic route to (S)-2-hydroxy-2'-(3-phenyluryl-benzyl)-1,1'-binaphthyl-3-carboxaldehyde (1), capable of recognizing tryptophan by fluorescence has been developed. The binol carboxaldehyde 1 exhibited a high selectivity to L-tryptophan over other examined L-${\alpha}$-amino acids such as alanine, phenylalanine, glutamine, arginine, lysine, serine, threonine, aspartat, valine, histidine and cysteine, with a fluorescence "turn-on" signal. In addition, 1 displayed chiral discrimination with good enantioselectivity toward L-tryptophan over D-tryptophan through different fluorescence enhancement factors.