11/05/2013  TCI eNewsletter

Synthetic Organic Chemistry

Research Article

Synthesis of Optically Active Piperidines by Enantioselective Addition Reaction

Almqvist et al. have reported the synthesis of optically active piperidines by enantioselective addition of aryl Grignard reagents to pyridine N-oxides followed by reduction. According to their results, the addition reactions proceed enantioselectively to give N-hydroxytetrahydropyridines by using Li-(+)-BINOL-ate, which is generated from (R)-(+)-BINOL and phenyl lithium, as a chiral ligand. Subsequent reduction affords optically active piperidines in high yields with high optical purities. BINOL is both easily removed and recovered from the crude reaction mixture.


M. Hussain, T. S.-L. Banchelin, H. Andersson, R. Olsson, F. Almqvist, Org. Lett. 2013, 15, 54.

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Product Highlight

Hapten Labeling Reagent Having Antigenicity but not Provoking an Immune Response

In 1920s and 1930s, K. Landsteiner et al. revealed that antibodies are raised against organic small molecules when an animal is injected with the biological protein combined with organic small molecules which are ordinarily non-antigenic.1) The antibodies produced independently of an antibody against the protein, show an antigen-antibody reaction with small molecules, but do not provoke an immune response. Aromatic compounds like dinitrophenol (1), and sugars are known as the small molecules called "haptens (incomplete antigens)".
N-Succinimidyl 6-(2,4-dinitroanilino)hexanoate (2) is a hapten-labeling reagent containing the 2,4-dinitrophenyl group (DNP). 2 can bind covalently to an amino group of peptides and proteins, etc. via the succinimidyl moiety. The combination of labeled compounds and an anti-DNP antibody is applied to radioimmunoassay, ELISA, and immunohistochemical staining.2) Furthermore, research has also been reported on drug delivery systems (DDS) by using synthetic macromolecules labeled with 2,3) and on cell-surface receptor models incorporating 2.4)


1) a) K. Landsteiner, Biochem. Z. 1921, 119, 294.
    b) K. Landsteiner, J. Jacobs, J. Exp. Med. 1936, 64, 625.
2) a) J.-M. Le Doussal, M. Martin, E. Gautherot, M. Delaage, J. Barbet, J. Nucl. Med. 1989, 30, 1358.
    b) M. Mammen, F. A. Gomez, G. M. Whitesides, Anal. Chem. 1995, 67, 3526.
    c) E. W. Olle, A. Sreekumar, R. L. Warner, S. D. McClintock, A. M. Chinnaiyan, M. R. Bleavins, T. D. Anderson, K. J. Johnson,
       Mol. Cell. Proteomics 2005, 4, 1664.
    d) G. V. Kalayda, G. Zhang, T. Abraham, H. J. Tanke, J. Reedijk, J. Med. Chem. 2005, 48, 5191.
3) R. S. Burke, S. H. Pun, Bioconjugate Chem. 2008, 19, 693.
4) S. Boonyarattanakalin, S. E. Martin, S. A. Dykstra, B. R. Peterson, J. Am. Chem. Soc. 2004, 126, 16379.

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Mixed-Mode (ODS+Ion-Exchange) HPLC Columns “TCI Dual”

TCI supplies six types of Mixed-Mode columns for acidic and basic samples.
They have both reversed phase (ODS) function and ion-exchange function. Based on the character of the analyte, suitable column can be chosen.

Recommended Cases for Mixed-Mode Columns
・Non retentive samples by ODS column
・Samples that are contained both hydrophobic and acidic (or basic ) compounds
・Do not want to use ion-pair reagent
・Different separation pattern is required instead of ODS's result
TCI Dual

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For more details of the product search function, please visit TCI website.

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