Advanced Synthesis and Catalysis p. 3297 - 3304 (2021)
Update date:2022-08-04
Topics:
Song, Liangliang
Ojeda-Carralero, Gerardo M.
Parmar, Divyaakshar
González-Martínez, David A.
Van Meervelt, Luc
Van der Eycken, Johan
Goeman, Jan
Rivera, Daniel G.
Van der Eycken, Erik V.
The field of peptide derivatization by metal-catalyzed C?H activation has been mostly directed to modify the side chains, but poor attention has been given to the peptide backbone. Here we report a ruthenium-catalyzed C?H activation/annulation process that can chemoselectively modify the peptide backbone producing functionalized isoquinolone scaffolds with high regioselectivity in a rapid and step-economical manner. This strategy is characterized by racemization-free conditions and the production of fluorescent peptides, and peptide conjugates to drugs, natural products and other peptide fragments, providing a chemical approach for the construction of novel peptide-pharmacophore conjugates. Mechanistic studies suggest that amide bonds of peptide backbone act as the bidentate directing group to promote the C?H activation/annulation process. This report provides an unprecedented example of peptide backbone diversification and bioorthogonal ligation exploiting the power of ruthenium-catalyzed C?H activation. (Figure presented.).
View MoreFOSHAN NANHAI ZHONGNAN PHARMACEUTICAL FACTORY
Contact:0086-0757-85609331
Address:XIAHENGTIAN INDUSTRIAL ZONE,SHAYONG VILLAGE,LISHUI TOWN
Xi'an Kaixiang Photoelectric Technology Co., Ltd
website:http://www.kxmaterials.com/
Contact:86-29-15991651477
Address:Building 6, Biopharmaceutical Industry R&D Cluster Base, No. 16, Caotang 4th Road, Caotang Science and Technology Industrial Base, High-tech Zone, Xi'an City, Shaanxi Province, China
Wuhan Konberd Biotech Co., Ltd.
Contact:+86-27-87205925
Address:NO.666, Gaoxin Road, Eastlake High-tech zone
Beijing Mediking Biopharm Co., Ltd.
Contact:+86-10-89753524/81760121/81769521
Address:Hongxianghong Incubator, Beiqijia Town, Changping district, Beijing, China
Hefei Highzone Fine Chemical S&T CO.,LTD
Contact:86-0551-63663560
Address:room 1801 NO. 24 Shuguang RD.
Doi:10.1021/jm100812a
(2010)Doi:10.1016/S0040-4020(99)00588-8
(1999)Doi:10.1016/S0968-0896(01)00132-8
(2001)Doi:10.1021/acs.orglett.9b02248
(2019)Doi:10.1080/15257779908041505
(1999)Doi:10.1055/s-1999-3614
(1999)