An Approach for Simultaneous Synthesis of cis- and trans-3-Substituted Proline-Glutamic Acid Chimeras

作者：Maity Jyotirmoy^*; Saha Pinaki; Gerling Ulla I M; Lentz Dieter; Koksch Beate

来源：Synthesis, 2012, 44(19): 3063-3070.

DOI：10.1055/s-0032-1316986

• benzyl 4-oxo-N-(9-phenylfluoren-9-yl) proline ester
• alkylation
• cis- and trans-3-substituted proline-glutamic acid chimeras
• Fmoc-amino acid
• peptides

Synthesis of cis- and trans-3-substituted proline-glutamic acid chimeras with suitable protection for peptide synthesis through Fmoc-strategy was accomplished in six steps from benzyl (2S)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate, which had been synthesized from trans-4-hydroxyproline in three steps. This methodology involved generation of cis- and trans-3-alkylated proline moieties, and manipulation of functionality and protecting groups to obtain proline-chimera monomers in appropriate form for peptide synthesis.

• 出版日期2012-10