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Synfacts 2008(10): 1110-1110  
DOI: 10.1055/s-2008-1078193
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Solid-Phase Fluorescent Labeling of Receptor Ligands by Click Reaction

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Hidetoshi Ohta
D. Bonnet*, S. Riché, S. Loison, R. Dagher, M.-C. Frantz, L. Boudier, R. Rahmeh, B. Mouillac, J. Haiech, M. Hibert
Université Strasbourg 1 and Université Montpellier I et II, France
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

Solid-phase fluorescent labeling of biologically active 1-benzazepine derivatives by 1,3-dipolar cycloaddition reaction is described. Thus, resin-bound 1-benzazepine 6 was prepared from DFPE resin 1 through the solid-phase reductive amination and amide bond forming reactions. Then, Cu(I)-catalyzed 1,3-cycloaddition of resin 6 with lissamine-(ethylene glycol)3-azido 7 followed by treatment of the resin with TFA gave the fluorescent-labeled benzazepine 8 as a mixture of ortho- and para-lissamine isomers (ortho:para = 1:1.6). After RP-HPLC purification, the ortho and para isomers were obtained in 16 and 28% overall yields, respectively.