Peptide Cyclization by the Use of Acylammonium Species.
Continuous Flow
Cyclization
Natural Products
Peptides
Specialty Peptides
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
03 07 2023
03 07 2023
Historique:
received:
13
01
2023
medline:
29
6
2023
pubmed:
10
5
2023
entrez:
10
5
2023
Statut:
ppublish
Résumé
Although cyclic peptides have become increasingly important as drugs, the most conventional peptide cyclization method using moderately active coupling agents suffers from a lot of waste and high cost as well as long reaction times and burdensome purification. Herein, we report an unconventional approach to peptide cyclization that uses acylammonium species generated from inexpensive and less wasteful Me
Identifiants
pubmed: 37161693
doi: 10.1002/anie.202300647
doi:
Substances chimiques
Peptides
0
Peptides, Cyclic
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300647Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
For recent selected reviews that describe importance of cyclic peptide based drugs, see:
A. A. Vinogradov, Y. Yin, H. Suga, J. Am. Chem. Soc. 2019, 141, 4167-4181;
X. Jing, K. Jin, Med. Res. Rev. 2020, 40, 753-810;
H. Zhang, S. Chen, RSC Chem. Biol. 2022, 3, 18-31.
C. Jayanta, R. Florian, K. Horst, Angew. Chem. Int. Ed. 2013, 52, 254-269.
For selected reviews on chemical peptide cyclization, see:
C. J. White, A. K. Yudin, Nat. Chem. 2011, 3, 509-524;
A. El-Faham, F. Albericio, Chem. Rev. 2011, 111, 6557-6602;
F. Albericio, A. El-Faham, Org. Process Res. Dev. 2018, 22, 760-772;
V. Sarojini, A. J. Cameron, K. G. Varnava, W. A. Denny, G. Sanjayan, Chem. Rev. 2019, 119, 10318-10359.
F. Albericio, J. M. Bofill, A. El-Faham, S. A. Kates, J. Org. Chem. 1998, 63, 9678-9683.
J. Magano, Org. Process Res. Dev. 2022, 26, 1562-1689.
A. Isidro-Llobet, M. N. Kenworthy, S. Mukherjee, M. E. Kopach, K. Wegner, F. Gallou, A. G. Smith, F. Roschangar, J. Org. Chem. 2019, 84, 4615-4628.
R. A. Boissonnas, Helv. Chim. Acta 1951, 34, 874-879;
J. R. Vaughan, J. Am. Chem. Soc. 1951, 73, 3547;
T. Wieland, H. Bernhard, Justus Liebigs Ann. Chem. 1951, 572, 190-194.
T. Wieland, J. Faesel, H. Faulstich, Justus Liebigs Ann. Chem. 1968, 713, 201-208;
T. Wieland, J. Faesel, W. Konz, Justus Liebigs Ann. Chem. 1969, 722, 197-209;
H. Faulstich, E. Nebelin, T. Wieland, Justus Liebigs Ann. Chem. 1973, 1973, 50-58;
L. Tomasic, G. P. Lorenzi, Helv. Chim. Acta 1987, 70, 1012-1016;
G. C. Zanotti, B. E. Campbell, K. R. K. Easwaran, E. R. Blout, Int. J. Pept. Protein Res. 1988, 32, 527-535;
G. Zanotti, F. Rossi, M. Saviano, T. Tancredi, G. Saviano, A. Maione, M. Filizola, B. Di Blasio, C. Pedone, J. Am. Chem. Soc. 1995, 117, 8651-8658;
A. D‘Ursi, S. Albrizio, C. Fattorusso, A. Lavecchia, G. Zanotti, P. A. Temussi, J. Med. Chem. 1999, 42, 1705-1713.
R. A. Boissonnas, I. Schumann, Helv. Chim. Acta 1952, 35, 2229-2235.
S. Fuse, Y. Mifune, T. Takahashi, Angew. Chem. Int. Ed. 2014, 53, 851-855;
S. Fuse, Y. Mifune, H. Nakamura, H. Tanaka, Nat. Commun. 2016, 7, 13491;
Y. Mifune, H. Nakamura, S. Fuse, Org. Biomol. Chem. 2016, 14, 11244-11249;
S. Fuse, K. Masuda, Y. Otake, H. Nakamura, Chem. Eur. J. 2019, 25, 15091-15097;
Y. Otake, Y. Shibata, Y. Hayashi, S. Kawauchi, H. Nakamura, S. Fuse, Angew. Chem. Int. Ed. 2020, 59, 12925-12930.
S. Fuse, K. Komuro, Y. Otake, H. Masui, H. Nakamura, Chem. Eur. J. 2021, 27, 7525-7532.
J.-i. Yoshida, Flash Chemistry-Fast Organic Synthesis in Micro Systems, Wiley-VCH, Weinheim, 2008;
J.-i. Yoshida, A. Nagaki, T. Yamada, Chem. Eur. J. 2008, 14, 7450-7459.
D. J. Brunelle, E. P. Boden, Makromol. Chem. Macromol. Symp. 1992, 54-5, 397-412.
H. Mayr and co-workers reported higher nucleophilicity parameters for secondary amines (Me2NH in MeCN: 17.96, MeHNCH2CN in H2O: 13.50) compared with that of corresponding primary amines (MeNH2 in MeCN: 15.19, H2NCH2CN in H2O: 12.29).
T. A. Nigst, A. Antipova, H. Mayr, J. Org. Chem. 2012, 77, 8142-8155;
F. Brotzel, Y. C. Chu, H. Mayr, J. Org. Chem. 2007, 72, 3679-3688.
Y.-R. Zhao, X.-K. Wang, J. Zhou, C.-X. Cheng, X.-L. Huang, H.-M. Wu, Chin. J. Chem. 1995, 13, 552-557.
J. Han, M. Huang, Z. Wang, Y. Zheng, G. Zeng, W. He, N. Tan, J. Pept. Sci. 2015, 21, 550-553.
A. D. Curzons, D. J. C. Constable, D. N. Mortimer, V. L. Cunningham, Green Chem. 2001, 3, 1-6.
S. Zhang, Z. Amso, L. M. De Leon Rodriguez, H. Kaur, M. A. Brimble, J. Nat. Prod. 2016, 79, 1769-1774.
J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243-2266.
R. Chen, Z. Cheng, J. Huang, D. Liu, C. Wu, P. Guo, W. Lin, RSC Adv. 2017, 7, 49235-49243.
L. Posada, G. Serra, Tetrahedron Lett. 2019, 60, 151281.
B. Liebermann, W. Ihn, E. Baumann, D. Tresselt, Phytochemistry 1988, 27, 357-359.
R. Sato, K. Oyama, H. Konno, Tetrahedron 2018, 74, 6173-6181.