Interplay of Pyrrolidine Units with Homo/Hetero Chirality and CF 3 -Aryl Substituents on Secondary Structures of β-Proline Tripeptides in Solution

All possible variants of β-proline functionalized tripeptides consisting of homo/hetero chiral monomeric all- 5-arylpyrrolidine-2,4-dicarboxylate units were synthesized for the first time by a nonpeptidic coupling method based on 1,3-dipolar cycloaddition chemistry of azomethine ylides. Secondary st...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-07, Vol.85 (14), p.8865-8871
Main Authors: Mantsyzov, Alexey B, Sokolov, Mikhail N, Ivantcova, Polina M, Bräse, Stefan, Polshakov, Vladimir I, Kudryavtsev, Konstantin V
Format: Article
Language:English
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Summary:All possible variants of β-proline functionalized tripeptides consisting of homo/hetero chiral monomeric all- 5-arylpyrrolidine-2,4-dicarboxylate units were synthesized for the first time by a nonpeptidic coupling method based on 1,3-dipolar cycloaddition chemistry of azomethine ylides. Secondary structures of β-proline tripeptides in solution were determined using the NMR spectroscopy data. -(Trifluoromethyl)phenyl substituent contributes to stereoselectivity of 1,3-dipolar cycloaddition and structural features of β-proline tripeptides. A β-proline CF -tripeptide with alternating absolute chirality between adjacent pyrrolidine units mimics natural PPII helix secondary structure.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00598