Organic Letters, volume 17, issue 24, pages 6178-6181
Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers
Kudryavtsev Konstantin V.
1, 2
,
Muhle-Goll Claudia
3
,
Sokolov Mikhail N
1
,
Dyuba Artem V
5
,
Arutyunyan Alexander M.
5
,
Howard Judith A.
6
,
Yu Chia-Chun
7
,
Guh Jih-Hwa
7
,
Zefirov Nikolay S.
1, 2
,
Bräse Stefan
3, 8
Publication type: Journal Article
Publication date: 2015-12-01
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
To produce a novel class of structurally ordered poly-β-prolines, an emergent method for synthesizing chiral β-peptide molecular frameworks was developed based on 1,3-dipolar cycloaddition chemistry of azomethine ylides. Functionalized short β-peptides with up to six monomeric residues were efficiently synthesized in homochiral forms using a cycloadditive oligomerization approach. X-ray, NMR, and CD structural analyses of the novel β-peptides revealed secondary structure features that were generated primarily by Z/E-β-peptide bond isomerism. Anticancer in cellulo activity of the new β-peptides toward hormone-refractory prostate cancer cells was observed and was dependent on the absolute configuration of the stereogenic centers and the chain length of the β-proline oligomers.
Citations by journals
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Organic Letters
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2 publications, 15.38%
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Acta Crystallographica Section E: Crystallographic Communications
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1 publication, 7.69%
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Journal of Organic Chemistry
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1 publication, 7.69%
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1 publication, 7.69%
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International Journal of Molecular Sciences
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International Journal of Molecular Sciences
1 publication, 7.69%
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Molecules
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1 publication, 7.69%
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European Journal of Organic Chemistry
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European Journal of Organic Chemistry
1 publication, 7.69%
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Chirality
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1 publication, 7.69%
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ChemistrySelect
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ChemistrySelect
1 publication, 7.69%
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Journal of Physical Chemistry B
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1 publication, 7.69%
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Journal of the American Chemical Society
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Journal of the American Chemical Society
1 publication, 7.69%
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Synthesis
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1 publication, 7.69%
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1
2
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Citations by publishers
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1
2
3
4
5
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American Chemical Society (ACS)
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American Chemical Society (ACS)
5 publications, 38.46%
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Wiley
|
Wiley
3 publications, 23.08%
|
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Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 15.38%
|
|
International Union of Crystallography (IUCr)
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International Union of Crystallography (IUCr)
1 publication, 7.69%
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Frontiers Media S.A.
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Frontiers Media S.A.
1 publication, 7.69%
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Thieme
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Thieme
1 publication, 7.69%
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1
2
3
4
5
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Kudryavtsev K. V. et al. Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers // Organic Letters. 2015. Vol. 17. No. 24. pp. 6178-6181.
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Kudryavtsev K. V., Ivantcova P. M., Muhle-Goll C., Churakov A. V., Sokolov M. N., Dyuba A. V., Arutyunyan A. M., Howard J. A., Yu C., Guh J., Zefirov N. S., Bräse S. Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers // Organic Letters. 2015. Vol. 17. No. 24. pp. 6178-6181.
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TY - JOUR
DO - 10.1021/acs.orglett.5b03154
UR - https://doi.org/10.1021%2Facs.orglett.5b03154
TI - Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers
T2 - Organic Letters
AU - Dyuba, Artem V
AU - Arutyunyan, Alexander M.
AU - Yu, Chia-Chun
AU - Zefirov, Nikolay S.
AU - Kudryavtsev, Konstantin V.
AU - Ivantcova, Polina M.
AU - Muhle-Goll, Claudia
AU - Churakov, Andrei V.
AU - Sokolov, Mikhail N
AU - Howard, Judith A.
AU - Guh, Jih-Hwa
AU - Bräse, Stefan
PY - 2015
DA - 2015/12/01 00:00:00
PB - American Chemical Society (ACS)
SP - 6178-6181
IS - 24
VL - 17
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2015_Kudryavtsev,
author = {Artem V Dyuba and Alexander M. Arutyunyan and Chia-Chun Yu and Nikolay S. Zefirov and Konstantin V. Kudryavtsev and Polina M. Ivantcova and Claudia Muhle-Goll and Andrei V. Churakov and Mikhail N Sokolov and Judith A. Howard and Jih-Hwa Guh and Stefan Bräse},
title = {Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021%2Facs.orglett.5b03154},
number = {24},
pages = {6178--6181},
doi = {10.1021/acs.orglett.5b03154}
}
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MLA
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Kudryavtsev, Konstantin V., et al. “Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers.” Organic Letters, vol. 17, no. 24, Dec. 2015, pp. 6178-6181. https://doi.org/10.1021%2Facs.orglett.5b03154.
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