Metal-free sp
Brevianamide F
C−H activation
Metal-free borylation
Oglufanide
Tryptophan borylation
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
01 Dec 2023
01 Dec 2023
Historique:
revised:
06
10
2023
received:
20
07
2023
medline:
4
12
2023
pubmed:
17
10
2023
entrez:
17
10
2023
Statut:
ppublish
Résumé
The discovery of milder and robust strategies to enable the introduction of organoboronates in peptides remains conspicuously underdeveloped. Herein, we demonstrate an efficient method for the site-selective sp
Identifiants
pubmed: 37847482
doi: 10.1002/asia.202300638
doi:
Substances chimiques
Tryptophan
8DUH1N11BX
Peptides
0
Biological Products
0
Metals
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300638Subventions
Organisme : Department of Science & Technology
Organisme : DST-SERB
ID : CRG/2021/005541
Organisme : Council for Scientific and Industrial Research (CSIR)
Organisme : University Grants Commission (UGC)
Organisme : CDRI SAIF
Organisme : CDRI
ID : 10685
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
J. N. deGruyter, L. R. Malins, P. S. Baran, Biochemistry 2017, 56, 3863-3873.
A. F. M. Noisier, M. A. Brimble, Chem. Rev. 2014, 114, 8775-8806.
S. J. Tower, W. J. Hetcher, T. E. Myers, N. J. Kuehl, M. T. Taylor, J. Am. Chem. Soc. 2020, 142, 9112-9118.
H. Gruß, N. Sewald, Chem. Eur. J. 2020, 26, 5328-5340.
L. Mendive-Tapia, S. Preciado, J. García, R. Ramón, N. Kielland, F. Albericio, R. Lavilla, Nat. Commun. 2015, 6, 7160.
L. Xu, C. Zhang, Y. He, L. Tan, D. Ma, Angew. Chem. Int. Ed. 2016, 55, 321-325.
A. Schischko, H. Ren, N. Kaplaneris, L. Ackermann, Angew. Chem. Int. Ed. 2017, 56, 1576-1580.
Y. Wang, J. B. Gloer, J. A. Scott, D. Malloch, J. Nat. Prod. 1995, 58, 93-99.
Y. Imai, K. J. Meyer, A. Iinishi, Q. Favre-Godal, R. Green, S. Manuse, M. Caboni, M. Mori, S. Niles, M. Ghiglieri, C. Honrao, X. Ma, J. J. Guo, A. Makriyannis, L. Linares-Otoya, N. Böhringer, Z. G. Wuisan, H. Kaur, R. Wu, A. Mateus, A. Typas, M. M. Savitski, J. L. Espinoza, A. O′Rourke, K. E. Nelson, S. Hiller, N. Noinaj, T. F. Schäberle, A. D′Onofrio, K. Lewis, Nature 2019, 576, 459-464.
N. A. Isley, Y. Endo, Z. C. Wu, B. C. Covington, L. B. Bushin, M. R. Seyedsayamdost, D. L. Boger, J. Am. Chem. Soc. 2019, 141, 17361-S17369.
J. Garfunkle, F. S. Kimball, J. D. Trzupek, S. Takizawa, H. Shimamura, M. Tomishima, D. L. Boger, J. Am. Chem. Soc. 2009, 131, 16036-16038.
J. A. Swain, S. R. Walker, M. B. Calvert, M. A. Brimble, Nat. Prod. Rep. 2022, 39, 410-443.
T. A. Shah, P. B. De, S. Pradhan, T. Punniyamurthy, Chem. Commun. 2019, 55, 572-587.
I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890-931.
J. F. Hartwig, Chem. Soc. Rev. 2011, 40, 1992-2002.
M.-A. Légaré, M.-A. Courtemanche, É. Rochette, F.-G. Fontaine, Science 2015, 349, 513-516.
N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722-6737.
A. Ros, R. Fernández, J. M. Lassaletta, Chem. Soc. Rev. 2014, 43, 3229-3243.
Y. Li, X.-F. Wu, Angew. Chem. Int. Ed. 2020, 59, 1770-1774.
M. Hassan, S. Guria, S. Dey, J. Das, B. Chattopadhyay, Sci. Adv. 2023, 9, eadg3311.
C. Li, J. Wang, L. M. Barton, S. Yu, M. Tian, D. S. Peters, M. Kumar, A. W. Yu, K. A. Johnson, A. K. Chatterjee, Science 2017, 356, eaam7355.
Y. Feng, D. Holte, J. Zoller, S. Umemiya, L. R. Simke, P. S. Baran, J. Am. Chem. Soc. 2015, 137, 10160-10163.
R. P. Loach, O. S. Fenton, K. Amaike, D. S. Siegel, E. Ozkal, M. Movassaghi, J. Org. Chem. 2014, 79, 11254-11263.
V. A. Kallepalli, F. Shi, S. Paul, E. N. Onyeozili, R. E. Jr. Maleczka, M. R. Smith, J. Org. Chem. 2015, 80(16), 8341-8353.
F. Shen, S. Tyagarajan, D. Perera, S. W. Krska, P. E. Maligres, M. R. Smith, R. E. Jr. Maleczka, Org. Lett. 2016, 18, 1554-1557.
D. W. Robbins, T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 4068-4069.
S. A. Iqbal, J. Cid, R. J. Procter, M. Uzelac, K. Yuan, M. J. Ingleson, Angew. Chem. Int. Ed. 2019, 58, 15381-15385.
J. Lv, X. Chen, X. S. Xue, B. Zhao, Y. Liang, M. Wang, L. Jin, Y. Yuan, Y. Han, Y. Zhao, Y. Lu, J. Zhao, W. Y. Sun, K. N. Houk, Z. Shi, Nature 2019, 575, 336-340.
Z. J. Wang, X. Chen, L. Wu, J. J. Wong, Y. Liang, Y. Zhao, K. N. Houk, Z. Shi, Angew. Chem. Int. Ed. 2021, 60, 8500-8504.
S. Rej, A. Das, N. Chatani, Chem. Sci. 2021, 12, 11447-11454.
J. Lv, B. Zhao, Y. Yuan, Y. Han, Z. Shi, Nat. Commun. 2020, 11, 1316.
Optimal protocol for the metal-free C7 borylation of Phth-Trp(Piv)-OMe: To a cold solution (0 °C) of Phth-Trp(Piv)-OMe (1 mmol) in dry DCM (5 mL) under nitrogen atmosphere added solution of BBr3 (1 M in DCM, 2.2 mL, 2.2 mmol). The reaction mixture was stirred at 0 °C for 1 h and then treated with a pinacol (3 mmol) and pyridine or DBU (3 mmol). The reaction mixture was allowed to warm to ambient temperature and continued to stir further 1 h. The solvent was removed under a vacuum and the crude product was purified by silica gel column chromatography using EtOAc : Hexane (1 : 5), obtained C7-borylated compound Phth-Trp(N-Piv)(C7-BPin)-OMe.
Optimal protocol to obtained Phth-Trp(Piv)(C7-Bpin)-OH: To a cold solution (0 °C) of Phth-Trp(Piv)-OMe (1 mmol) in dry DCM (5 mL) under nitrogen atmosphere added solution of BBr3 (1 M in DCM, 2.2 mL, 2.2 mmol). The reaction mixture was stirred at 25 °C for 1 h and then treated with a pinacol (3 mmol) and pyridine or DBU (3 mmol). The reaction mixture was continued to stir further 1 h and then added 5% NaHCO3 dropwise to the reaction mixture till pH-8 to make sodium salt of ester hydrolyzed. Then washed with diethylether (10 mL) and then the aqueous part acidified (till pH-2) with 4 N HCl. Extracted with ethyl acetate, dried over Na2SO4 and concentrated under reduced pressure to get the desired C7-borylated compound Phth-Trp(N-Piv)(C7-BPin)-OH.
G. B. Fields, Methods Mol. Biol. 1994, 35, 17-27.
J. Quer, M. Buti, M. Cubero, J. Guardia, R. Esteban, J. I. Esteban, Infect. Drug Resist. 2010, 3, 133-145.
M. Ruiz, J. D. Sanchez, P. L. Alvarado, J. C. Menendez, Tetrahedron. 2012, 68, 705-710.
Y. Yu, Y. Zhou, Z. Song, G. Liang, Org. Biomol. Chem. 2018, 16, 4958-4962.
K. Bartosik, E. Sochacka, G. Leszczynska, Org. Biomol. Chem. 2017, 15, 2097-2103.
B. Elchert, J. Li, J. Wang, Y. Hui, R. Rai, R. Ptak, P. Ward, J. Y. Takemoto, M. Bensaci, C. Chang, J. Org. Chem. 2004, 69, 1513-1523.
K. Masahiro, I. Hidetoshi, S. Junichi, K. Minoru, O. Tetsuji, Chem. Pharm. Bull. 2016, 64, 1009-1018.
R. Ben Ameur Mehdi, K. A. Shaaban, I. K. Rebai, S. Smaoui, S. Bejara, L. Mellouli, Nat. Prod. Res. 2009, 23, 1095-1107.
J. F. Sanz-Cervera, E. M. Stocking, T. Usui, H. Osada, R. M. Williams, Bioorg. Med. Chem. 2000, 8, 2407-2415.
W. Haishan, U. Takeo, O. Hiroyuki, A. Ganesan, J. Med. Chem. 2000, 43(8), 1577-1585.
M. Toumi, C. Frois, Je. Marrot, G. Evano, Org. Lett. 2008, 10, 5027-5030.
B. S. Jursic, P. K. Patel, Carbohydr. Res. 2006, 341, 2858-2866.
B. Wei, D. Xie, S. Lai, Y. Jiang, H. Fu, D. Wei, B. Han, Angew. Chem. Int. Ed. 2021, 60, 3182-3183.
R. P. Loach, O. S. Fenton, K. Amaike, D. S. Siegel, E. Ozkal, M. Movassaghi, J. Org. Chem. 2014, 79, 11254-11263.
T. Kato, S. Kuriyama, K. Nakajima, Y. Nishibayash, Chem. Asian J. 2019, 14, 2097-2101.
L. Xu, G. Wang, S. Zhang, H. Wang, L. Wang, L. Liu, J. Jiao, P. Li, Tetrahedron 2017, 73, 7123-7157.