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Synfacts 2009(12): 1417-1417  
DOI: 10.1055/s-0029-1218194
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Peptidyl Thioacid Synthesis with 9-Fluorenylmethyl Thiol-Linked Resin

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Hidetoshi Ohta
D. Crich*, K. Sana
Centre National de la Recherche Scientifique, Gif-sur-Yvette, France and Wayne State University, Detroit, USA
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

A solid-phase synthesis of peptidyl thioacids 10 with a resin-bound 9-fluorenylmethyl thiol 8 is described. Thus, (9H-fluoren-2-yl)carb­amic acid t-butyl ester (1) was converted into the resin-supported thiol 8 in ten steps. The Boc-based SPPS (solid-phase peptide synthesis) was carried out with 8 and N-Boc-protected amino acids to afford the resin-bound peptidyl thioesters 9. Treatment of 9 with piperidine gave the corresponding peptidyl thioacids 10 in 55-95% yield.