Journal of Organic Chemistry, volume 85, issue 14, pages 8865-8871

Interplay of Pyrrolidine Units with Homo/Hetero Chirality and CF3-Aryl Substituents on Secondary Structures of β-Proline Tripeptides in Solution

Publication typeJournal Article
Publication date2020-06-11
Quartile SCImago
Q1
Quartile WOS
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Impact factor3.6
ISSN00223263, 15206904
Organic Chemistry
Abstract
All possible variants of β-proline functionalized tripeptides consisting of homo/hetero chiral monomeric all-cis 5-arylpyrrolidine-2,4-dicarboxylate units were synthesized for the first time by a non-peptidic 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. o-(Trifluoromethyl)phenyl substituent contributes to stereoselectivity of 1,3-dipolar cy-cloaddition and structural features of β-proline tripeptides. A β-proline CF3-tripeptide with alternating absolute chirality between adjacent pyrrolidine units mimics natural PPII helix secondary structure.

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Journal of Physical Chemistry Letters
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American Chemical Society (ACS)
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American Chemical Society (ACS)
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Mantsyzov A. B. et al. Interplay of Pyrrolidine Units with Homo/Hetero Chirality and CF3-Aryl Substituents on Secondary Structures of β-Proline Tripeptides in Solution // Journal of Organic Chemistry. 2020. Vol. 85. No. 14. pp. 8865-8871.
GOST all authors (up to 50) Copy
Mantsyzov A. B., Sokolov M. N., Ivantcova P. M., Bräse S., Polshakov V. I., Kudryavtsev K. V. Interplay of Pyrrolidine Units with Homo/Hetero Chirality and CF3-Aryl Substituents on Secondary Structures of β-Proline Tripeptides in Solution // Journal of Organic Chemistry. 2020. Vol. 85. No. 14. pp. 8865-8871.
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TY - JOUR
DO - 10.1021/acs.joc.0c00598
UR - https://doi.org/10.1021%2Facs.joc.0c00598
TI - Interplay of Pyrrolidine Units with Homo/Hetero Chirality and CF3-Aryl Substituents on Secondary Structures of β-Proline Tripeptides in Solution
T2 - Journal of Organic Chemistry
AU - Mantsyzov, Alexey B.
AU - Kudryavtsev, Konstantin V.
AU - Sokolov, Mikhail N
AU - Ivantcova, Polina M.
AU - Bräse, Stefan
AU - Polshakov, Vladimir I.
PY - 2020
DA - 2020/06/11 00:00:00
PB - American Chemical Society (ACS)
SP - 8865-8871
IS - 14
VL - 85
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2020_Mantsyzov
author = {Alexey B. Mantsyzov and Konstantin V. Kudryavtsev and Mikhail N Sokolov and Polina M. Ivantcova and Stefan Bräse and Vladimir I. Polshakov},
title = {Interplay of Pyrrolidine Units with Homo/Hetero Chirality and CF3-Aryl Substituents on Secondary Structures of β-Proline Tripeptides in Solution},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021%2Facs.joc.0c00598},
number = {14},
pages = {8865--8871},
doi = {10.1021/acs.joc.0c00598}
}
MLA
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Mantsyzov, Alexey B., et al. “Interplay of Pyrrolidine Units with Homo/Hetero Chirality and CF3-Aryl Substituents on Secondary Structures of β-Proline Tripeptides in Solution.” Journal of Organic Chemistry, vol. 85, no. 14, Jun. 2020, pp. 8865-8871. https://doi.org/10.1021%2Facs.joc.0c00598.
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