Biomimetic α-selective ribosylation enables two-step modular synthesis of biologically important ADP-ribosylated peptides.

Biomimetic α-selective ribosylation enables two-step modular synthesis of biologically important ADP-ribosylated peptides.
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仿生 α 选择性核糖基化可实现生物学上重要的 ADP 核糖基化肽的两步模块化合成

DOI:
10.1038/s41467-020-19409-1
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发表时间:
2020-11-05
影响因子:
16.6
通讯作者:
Li L
Li L
中科院分区:
综合性期刊1区
文献类型:
--
作者:
Zhu A;Li X;Bai L;Zhu G;Guo Y;Lin J;Cui Y;Tian G;Zhang L;Wang J;Li XD;Li L

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The α-type ADP-ribosylated peptides represent a class of important molecular tools in the field of protein ADP-ribosylation, however, they are difficult to access because of their inherent complicated structures and the lack of effective synthetic tools. In this paper, we present a biomimetic α-selective ribosylation reaction to synthesize a key intermediate, α-ADP-ribosyl azide, directly from native β-nicotinamide adenine dinucleotide in a clean ionic liquid system. This reaction in tandem with click chemistry then offers a two-step modular synthesis of α-ADP-ribosylated peptides. These syntheses can be performed open air in eppendorf tubes, without the need for specialized instruments or training. Importantly, we demonstrate that the synthesized α-ADP-ribosylated peptides show high binding affinity and desirable stability for enriching protein partners, and reactivity in post-stage poly ADP-ribosylations. Owing to their simple chemistry and multidimensional bio-applications, the presented methods may provide a powerful platform to produce general molecular tools for the study of protein ADP-ribosylation. ADP-ribosylated peptides are important molecular tools, however, the lack of effective synthetic methods hinders the access to their complex structures. Here, the authors present a biomimetic α-selective ribosylation reaction coupled with click chemistry ultimately providing a two-step modular synthesis of α-ADP-ribosylated peptides.
在无金属条件下使用氧作为氧化剂通过氢键促进醇向酯的转化
DOI: 10.1126/sciadv.aas9319
发表时间: 2018-10
期刊: Science advances
影响因子: 13.6
作者:
Liu M;Zhang Z;Liu H;Xie Z;Mei Q;Han B
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DOI: 10.1111/j.1432-1033.1978.tb12730.x
发表时间: 1978-01-01
期刊: EUROPEAN JOURNAL OF BIOCHEMISTRY
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期刊: EMBO REPORTS
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