Green Synthesis and Catalysis

Regioselective syntheses of glycosides using modern chemical methods suffer from the need to invoke multiple steps of protection and deprotection, and even then product mixtures may occur. Discovering and tuning by mutagenesis glycosyltransferases (GTs) with considerable substrate promiscuity is an alternative challenge. We tuned by rational design based on extended Focused Rational Iterative Site-specific Mutagenesis (FRISM) a newly identified GT from Siraitia grosvenorii (UGT74AC2) as the catalyst in the targeted regioselective glucosylation of the polyhydroxy substrate silybin and derivatives. A handful of mutants was constructed with a restricted set of rationally chosen amino acids, providing variants showing 94%, > 99% and > 99% selectivity on the 3-OH, 7-OH and 3,7-O-diglycoside, respectively, compared with the wildtype resulting in a 22%:39%:39% product mixture. Remarkably, even N- and S-glucosylation was achieved. Docking and molecular dynamics (MD) simulations studies shed light on the origin of regioselectivity. These findings can be invoked to guide future enzymatic tailoring of UGTs in the production of flavonoids as potent pharmaceuticals and of other useful compounds.

Jiao Li

Ge Qu

Na Shang

Peng Chen

Yan Men

Weidong Liu

Zelong Mei

Yuanxia Sun

Zhoutong Sun

Near-perfect control of the regioselective glucosylation enabled by rational design of glycosyltransferases

理性设计糖基转移酶实现区域选择性糖基化的近乎完美控制

A dehydroxylative ring-opening Giese reaction of cyclobutanone oximes enabled by photoredox/Ti dual catalysis has been reported in this work. This protocol avoids the prefunctionalization of oximes and the use of stoichiometric triarylphosphine reagents. It also features mild conditions, broad substrate scope and good functional group tolerance. The gram-scale reaction, product derivatization, late-stage functionalization of complex pharmaceutical and natural product derivatives, and oligopeptide modification exhibit the potential application of this methodology in synthetic chemistry.

Huaigui Li

Yan Li

Weidong Yuan

Anling Qu

Kang Chen

Yingguang Zhu

Photoredox/Ti dual-catalyzed dehydroxylative ring-opening Giese reaction of cyclobutanone oximes

光氧化还原/钛双催化脱羟基开环Giese反应：环丁酮肟的研究

Shiqiang Mu

Qingqing Xuan

Yu Guo

Jian Xu

Qiuling Song

The synthesis of multi-substituted benzazepine derivatives via Mn(III)-promoted oxidative annulation of isocyanides with boronic acids

通过Mn(III)促进的异氰化物与硼酸的氧化环化合成多取代苯并氮杂卓衍生物

Xue-Yang Guo

Bo-Xuan Yao

Li-Rong Wen

Weisi Guo

Ming Li

Shao-Fei Ni

Lin-Bao Zhang

Regioselectively electrochemical Csp3-H alkoxylation for functionalized indanone

区域选择性电化学Csp3-H烷氧基化用于功能化茚满酮

We herein reported a sustainable synthesis of 3,3-disubstituted oxindoles via a Michael-type reaction based on the CuBr-catalysed capture of carboxylic oxonium ylides with isatylidene malononitrile. The reaction is characterized by a high atom economy and low economic constraints. The catalyst CuBr could be conveniently recyclized. The products of the reaction were found to be inhibitory against Na ion channels. We expect the reaction to shed the light on synthesis of biologically interesting molecules directed by principles of green chemistry.

Mengchu Zhang

Yukai Li

Yuwei Wang

Jirong Shu

Tianyuan Zhang

Dan Zhang

Song Cai

Taoda Shi

Wenhao Hu

A sustainable synthesis of 3,3-disubstituted oxindoles via CuBr-catalysed capture of carboxylic oxonium ylides with isatylidene malononitrile

通过CuBr催化的异吲哚啉亚甲基丙二腈捕获羧基氧鎓叶立德实现3,3-二取代异吲哚酮的可持续合成

Xinyue Lin

Chensi Li

Zeqin Zhuang

Chongxian Liang

Min Wu

Wei Yi

Zhi Zhou

Modular trifluoromethylselenolation and fluoroalkylselenolation via Ag(I)-mediated selenium nitrogen exchange reaction of benzothiaselenazole-1-oxides

通过Ag(I)介导的苯并噻二唑-1-氧化物硒氮交换反应实现模块化三氟甲基硒化及氟烷基硒化

Wujiu Jiang

Yuxing Tan

Penghui Ni

Yiyuan Peng

Yang Fu

Qiuping Ding

TFA-Catalyzed cascade annulation of thioamides with aromatic hydrazides/amines: an internal oxidant-triggered protocol to diverse N-heterocycles

三氟乙酸催化的硫酰胺与芳香肼/胺的级联环化反应：内源氧化剂触发的多样性N-杂环合成方法

Pan Zhou

Haoran Jiao

Yue Jing

Kaikai Niu

Hongjian Song

Yuxiu Liu

Qingmin Wang

Electrocatalytic regio- and stereoselective carboxylation of terminal alkynes with CO2

电催化区域和立体选择性羧基化末端炔烃与二氧化碳

Abbreviation	Green. Synth. Catal.
Journal Impact	8.12
Quartiles(Global)	CHEMISTRY, MULTIDISCIPLINARY(Q1)

ISSN	2666-5549
h-index	27

Publication Information	Publisher: KeAi Communications Co.，Publishing cycle: ，Journal Type: journal，Open Access Journals: Yes
Basic data	Year of publication: 2020，Proportion of original research papers: ，Self Citation Rate:， Gold OA Rate:
Journal Fees	$1000Details
Average review cycle	10 weeks

Green Synthesis and Catalysis

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Near-perfect control of the regioselective glucosylation enabled by rational design of glycosyltransferases

Photoredox/Ti dual-catalyzed dehydroxylative ring-opening Giese reaction of cyclobutanone oximes

The synthesis of multi-substituted benzazepine derivatives via Mn(III)-promoted oxidative annulation of isocyanides with boronic acids

Regioselectively electrochemical Csp3-H alkoxylation for functionalized indanone

A sustainable synthesis of 3,3-disubstituted oxindoles via CuBr-catalysed capture of carboxylic oxonium ylides with isatylidene malononitrile

The synthesis of multi-substituted benzazepine derivatives via Mn(III)-promoted oxidative annulation of isocyanides with boronic acids

Regioselectively electrochemical Csp3-H alkoxylation for functionalized indanone

Modular trifluoromethylselenolation and fluoroalkylselenolation via Ag(I)-mediated selenium nitrogen exchange reaction of benzothiaselenazole-1-oxides

TFA-Catalyzed cascade annulation of thioamides with aromatic hydrazides/amines: an internal oxidant-triggered protocol to diverse N-heterocycles

Electrocatalytic regio- and stereoselective carboxylation of terminal alkynes with CO2