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

Abstract

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.

Key words

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

• References

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