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 (2 S )-4-oxo-1-(9-phenyl-9 H -fluoren-9-yl)pyrrolidine-2-carboxylate, which had been synthesized from tra...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2012-10, Vol.44 (19), p.3063-3070
Main Authors: Maity, Jyotirmoy, Saha, Pinaki, Gerling, Ulla I. M., Lentz, Dieter, Koksch, Beate
Format: Article
Language:English
Subjects:
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Noncondensed benzenic compounds
Organic chemistry
Peptides
Preparations and properties
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Summary: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 (2 S )-4-oxo-1-(9-phenyl-9 H -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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0032-1316986