Synthesis of β3-Homophenylalanine-Derived Amino Acids and Peptides by Suzuki Coupling in Solution and on Solid Support

✍ Scribed by Michael Limbach; Markus Löweneck; Jürg V. Schreiber; Jens Frackenpohl; Dieter Seebach; Andreas Billich

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: German
• Weight: 267 KB
• Volume: 89
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200690143

✦ Synopsis

b-Peptides and, to a certain extent, also mixed a,b-peptides, are resistant to degradation by a variety of proteolytic enzymes that rapidly degrade natural a-peptides. This is one of many characteristics that make b-peptides an attractive class of compounds for drug-discovery studies. On the other hand, modern organometallic reactions such as the Suzuki-Miyaura cross-coupling have become standard tools in industry laboratories to derivatize side chains of a-peptidic compounds to build up libraries of unnatural peptides. Combining both features, we prepared (4-bromo)-b 3 -homophenylalanine derivatives 3 -5 and 12 as precursors for Suzuki-Miyaura couplings. From these bromo compounds, we synthesized biarylsubstituted b-homoamino acids 6, and analogs 13 and 15 of the anti-AIDS drug Saquinavir.