DMSO‐Triggered Complete Oxygen Transfer Leading to Accelerated Aqueous Hydrolysis of Organohalides under Mild Conditions

Liu, Haicheng; Liu, Jianping; Cheng, Xiaokai; Jia, Xiaojuan; Yu, Lei; Xu, Qing

doi:10.1002/cssc.201802138

Cited by 14 publications

(4 citation statements)

References 55 publications

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“…The synthesis of derivative 7 required the branched fatty acid 24 . Bromide 18 was converted to alcohol 23 with Cs 2 CO 3 and tetra- n -butylammonium iodide (TBAI) in DMSO and H 2 O . The TEMPO-mediated oxidation of alcohol 23 furnished the desired fatty acid 24 .…”

Section: Resultsmentioning

confidence: 99%

“…Bromide 18 was converted to alcohol 23 with Cs 2 CO 3 and tetran-butylammonium iodide (TBAI) in DMSO and H 2 O. 40 The TEMPO-mediated oxidation 41 of alcohol 23 furnished the desired fatty acid 24. The protected glycolipid 28 was obtained through condensation between fatty acid 24 and diol 27, which was prepared from glycosyl donor 12a through glycosylation and the removal of the acetal group.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Archaeal Glycerolipids Are Recognized by C-Type Lectin Receptor Mincle

et al. 2023

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Recently, various metabolites derived from host microbes have been reported to modulate the immune system, with potential involvement in health or diseases. Archaea, prokaryotic organisms, are present in the human body, but their connection with the host is largely unknown when compared to other microorganisms such as bacteria. This study focused on unique glycerolipids from symbiotic methanogenic archaea and evaluated their activities toward an innate immune receptor. The results revealed that archaeal lipids were recognized by the C-type lectin receptor Mincle and induced immune responses. A concurrent structure−activity relationship study identified the key structural features of archaeal lipids required for recognition by Mincle. Subsequent gene expression profiling suggested qualitative differences between the symbiotic archaeal lipid and the pathogenic bacteria-derived lipid. These findings have broad implications for understanding the function of symbiotic archaea in host health and diseases.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Archaeal Glycerolipids Are Recognized by C-Type Lectin Receptor Mincle

et al. 2023

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“…Bromide 18 was converted to alcohol 23 with Cs 2 CO 3 and TBAI in DMSO and H 2 O. [23] The TEMPO-mediated oxidation [24] of alcohol 23 furnished the desired fatty acid 24. The protected glycolipid 28 was obtained through condensation between fatty acid 24 and diol 27, which was prepared from glycosyl donor 12a through glycosylation and removal of the acetal group.…”

Section: Resultsmentioning

confidence: 99%

Archaeal glycerolipids are recognized by C-type lectin receptor Mincle

Oka

Watanabe

Ito

et al. 2022

Preprint

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Recently, various metabolites derived from host microbes have been reported to modulate the immune system, with potential involvement in health or diseases. Archaea, prokaryotic organisms, are present in the human body, but their connection with the host is largely unknown when compared with other microorganisms such as bacteria. This study focused on unique glycerolipids from symbiotic methanogenic archaea and evaluated their activities toward an innate immune receptor. The results revealed that archaeal lipids were recognized by the C-type lectin receptor Mincle and induced immune responses. A concurrent structure-activity relationship study identified key structural features of archaeal lipids required for recognition by Mincle. Subsequent gene expression profiling suggested qualitative differences between the symbiotic archaeal lipid and the pathogenic bacteria-derived lipid. These findings have broad implications for understanding the function and pathogenicity of symbiotic archaea to host health and diseases.

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“…The hydrolysis of alkyl halides is known as one of important laboratory synthetic methods for preparation of aliphatic alcohols. Traditional methods to aliphatic alcohols from aliphatic halides usually relied on a two-step procedure involving the use of nucleophilic oxygenated reagents such as acetate or formate, superoxide radical ions, and bis(tributyltin)oxide . Most of these approaches suffered from high temperature, the employment of dangerous reagents, and Ag catalysts.…”

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confidence: 99%

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Cai

Zhang

et al. 2019

Org. Lett.

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Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

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DMSO‐Triggered Complete Oxygen Transfer Leading to Accelerated Aqueous Hydrolysis of Organohalides under Mild Conditions

Cited by 14 publications

References 55 publications

Archaeal Glycerolipids Are Recognized by C-Type Lectin Receptor Mincle

Archaeal Glycerolipids Are Recognized by C-Type Lectin Receptor Mincle

Archaeal glycerolipids are recognized by C-type lectin receptor Mincle

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

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