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

Jyotirmoy Maity; Pinaki Saha; Ulla I. M. Gerling; Dieter Lentz; Beate Koksch

doi:10.1055/s-0032-1316986

Synthesis, Table of Contents

Synthesis 2012; 44(19): 3063-3070
DOI: 10.1055/s-0032-1316986

paper

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

Jyotirmoy Maity

^aInstitut für Chemie und Biochemie-Organische Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany

,

Pinaki Saha

^aInstitut für Chemie und Biochemie-Organische Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany

,

Ulla I. M. Gerling

^aInstitut für Chemie und Biochemie-Organische Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany

,

Dieter Lentz

^bInstitut für Chemie und Biochemie-Anorganische Chemie, Freie Universität Berlin, Fabeckstr. 34/36, 14195 Berlin, Germany, Fax: +49(30)83855644 Email: koksch@chemie.fu-berlin.de

,

Beate Koksch*

^aInstitut für Chemie und Biochemie-Organische Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany

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Abstract

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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

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References

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