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

Mantsyzov A.B., Sokolov M.N., Ivantcova P.M., Bräse S., Polshakov V.I., Kudryavtsev K.V.
Тип документа: Journal Article
Дата публикации: 2020-07-17
Название журнала: Journal of Organic Chemistry
Издатель: American Chemical Society
Квартиль по SCImago: Q1
Квартиль по Web of Science: Q1
Импакт-фактор 2021: 4.20
ISSN: 00223263, 15206904
DOI:  10.1021/acs.joc.0c00598
Organic Chemistry
Краткое описание
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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1. Mantsyzov A.B. и др. Interplay of Pyrrolidine Units with Homo/Hetero Chirality and CF3–Aryl Substituents on Secondary Structures of β-Proline Tripeptides in Solution // The Journal of Organic Chemistry. 2020. Т. 85. № 14. С. 8865–8871.
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TY - JOUR

DO - 10.1021/acs.joc.0c00598

UR - http://dx.doi.org/10.1021/acs.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 - The Journal of Organic Chemistry

AU - Mantsyzov, Alexey B.

AU - Sokolov, Mikhail N.

AU - Ivantcova, Polina M.

AU - Bräse, Stefan

AU - Polshakov, Vladimir I.

AU - Kudryavtsev, Konstantin V.

PY - 2020

DA - 2020/06/11

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,

doi = {10.1021/acs.joc.0c00598},

url = {https://doi.org/10.1021%2Facs.joc.0c00598},

year = 2020,

month = {jun},

publisher = {American Chemical Society ({ACS})},

volume = {85},

number = {14},

pages = {8865--8871},

author = {Alexey B. Mantsyzov and Mikhail N. Sokolov and Polina M. Ivantcova and Stefan Bräse and Vladimir I. Polshakov and Konstantin V. Kudryavtsev},

title = {Interplay of Pyrrolidine Units with Homo/Hetero Chirality and {CF}3{\textendash}Aryl Substituents on Secondary Structures of $\upbeta$-Proline Tripeptides in Solution}

}

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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.” The Journal of Organic Chemistry 85.14 (2020): 8865–8871. Crossref. Web.