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Synfacts 2007(8): 0882-0882  
DOI: 10.1055/s-2007-968806
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

p-Nitromandelic Acid Linked Peptide Synthesis

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada
A. Isidro-Llobet, M. Alvarez, K. Burger, J. Spengler*, F. Albericio*
Universitat de Barcelona, Spain and Universität Leipzig, Germany
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

p-Nitromandelic acid (Pnm) was used as a safety-catch linker for solid-phase synthesis of base-labile compounds of Boc/Bzl-protected depsipeptides. Thus, racemic Pnm protected with hexafluoroacetone (HFA-protected Pnm) was coupled with aminomethylated polystyrene resin (AM-resin) to give Pnm-AM-resin. Resin-supported depsipeptides 1 were then synthesized by the standard protocols for solid-phase peptide synthesis. The reduction of 1 with SnCl2/HCl followed by TFA treatment under microwave irradiation afforded depsipeptides 2 (purity: 18-82%; 13 examples).