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Late-stage C(sp2)–H and C(sp3)–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling
Chemical Science ( IF 8.4 ) Pub Date : 2020-03-24 , DOI: 10.1039/d0sc01260b Jun Wu 1, 2, 3, 4 , Nikolaos Kaplaneris 1, 2, 3, 4 , Shaofei Ni 1, 2, 3, 4 , Felix Kaltenhäuser 1, 2, 3, 4 , Lutz Ackermann 1, 2, 3, 4, 5
Chemical Science ( IF 8.4 ) Pub Date : 2020-03-24 , DOI: 10.1039/d0sc01260b Jun Wu 1, 2, 3, 4 , Nikolaos Kaplaneris 1, 2, 3, 4 , Shaofei Ni 1, 2, 3, 4 , Felix Kaltenhäuser 1, 2, 3, 4 , Lutz Ackermann 1, 2, 3, 4, 5
Affiliation
C(sp3)–H and C(sp2)–H glycosylations of structurally complex amino acids and peptides were accomplished through the assistance of triazole peptide-isosteres. The palladium-catalyzed peptide–saccharide conjugation provided modular access to structurally complex C-alkyl glycoamino acids, glycopeptides and C-aryl glycosides, while enabling the assembly of fluorescent-labeled glycoamino acids. The C–H activation approach represents an expedient and efficient strategy for peptide late-stage diversification in a programmable as well as chemo-, regio-, and diastereo-selective fashion.
中文翻译:
C-芳基/烷基糖肽的晚期C(sp2)–H和C(sp3)–H糖基化:机理研究和荧光标记
结构复杂的氨基酸和肽的C(sp 3)–H和C(sp 2)–H糖基化是通过三唑肽-等排物的协助完成的。钯催化的肽-糖共轭提供了结构上复杂的C-烷基糖氨基酸,糖肽和C-芳基糖苷的模块化通道,同时能够组装荧光标记的糖氨基酸。C–H活化方法代表了一种简便有效的肽后期多样化策略,可通过编程,化学,区域和非对映选择性方式进行。
更新日期:2020-03-24
中文翻译:
C-芳基/烷基糖肽的晚期C(sp2)–H和C(sp3)–H糖基化:机理研究和荧光标记
结构复杂的氨基酸和肽的C(sp 3)–H和C(sp 2)–H糖基化是通过三唑肽-等排物的协助完成的。钯催化的肽-糖共轭提供了结构上复杂的C-烷基糖氨基酸,糖肽和C-芳基糖苷的模块化通道,同时能够组装荧光标记的糖氨基酸。C–H活化方法代表了一种简便有效的肽后期多样化策略,可通过编程,化学,区域和非对映选择性方式进行。