In Vitro Production of Ergothioneine Isotopologues

被引：15

作者：

Beliaeva, Mariia A. ^{[1
]}

Burn, Reto ^{[1
]}

Lim, David ^{[1
]}

Seebeck, Florian P. ^{[1
]}

机构：

[1] Univ Basel, Dept Chem, Mattenstr 24a, CH-4002 Basel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 10期

关键词：

biocatalysis; ergothioneine; isotopes; methyltransferase; sulfur transferase; BIOSYNTHESIS; IDENTIFICATION; ANTIOXIDANT;

D O I：

10.1002/anie.202011096

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ergothioneine is an emerging component of the redox homeostasis system in human cells and in microbial pathogens, such as Mycobacterium tuberculosis and Burkholderia pseudomallei. The synthesis of stable isotope-labeled ergothioneine derivatives may provide important tools for deciphering the distribution, function, and metabolism of this compound in vivo. We describe a general protocol for the production of ergothioneine isotopologues with programmable H-2, N-15, C-13, S-34, and S-33 isotope labeling patterns. This enzyme-based approach makes efficient use of commercial isotope reagents and is also directly applicable to the synthesis of radio-isotopologues.

引用

页码：5209 / 5212

页数：4

共 40 条

[1] Prolonging healthy aging: Longevity vitamins and proteins [J].

Ames, Bruce N. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2018, 115 (43) :10836-10844

[2]

[Anonymous], 2018, ANGEW CHEM, V130, P1774, DOI 10.1002/ange.201704146

[3] Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences [J].

Atzrodt, Jens ;

Derdau, Volker ;

Kerr, William J. ;

Reid, Marc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (07) :1758-1784

[4] Metabolite Identification in Synechococcus sp. PCC 7002 Using Untargeted Stable Isotope Assisted Metabolite Profiling [J].

Baran, Richard ;

Bowen, Benjamin P. ;

Bouskill, Nicholas J. ;

Brodie, Eoin L. ;

Yannone, Steven M. ;

Northen, Trent R. .

ANALYTICAL CHEMISTRY, 2010, 82 (21) :9034-9042

[5] The biology of ergothioneine, an antioxidant nutraceutical [J].

Borodina, Irina ;

Kenny, Louise C. ;

McCarthy, Cathal M. ;

Paramasivan, Kalaivani ;

Pretorius, Etheresia ;

Roberts, Timothy J. ;

van der Hoek, Steven A. ;

Kell, Douglas B. .

NUTRITION RESEARCH REVIEWS, 2020, 33 (02) :190-217

[6]

Burn R., 2017, ANGEW CHEM, V129, P12682, DOI [10.1002/ange.201705932, DOI 10.1002/ANGE.201705932]

[7] Anaerobic Origin of Ergothioneine [J].

Burn, Reto ;

Misson, Laetitia ;

Meury, Marcel ;

Seebeck, Florian P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) :12508-12511

[8] Administration of Pure Ergothioneine to Healthy Human Subjects: Uptake, Metabolism, and Effects on Biomarkers of Oxidative Damage and Inflammation [J].

Cheah, Irwin K. ;

Tang, Richard M. Y. ;

Yew, Terry S. Z. ;

Lim, Keith H. C. ;

Halliwell, Barry .

ANTIOXIDANTS & REDOX SIGNALING, 2017, 26 (05) :193-206

[9] Single-Step Replacement of an Unreactive C-H Bond by a C-S Bond Using Polysulfide as the Direct Sulfur Source in the Anaerobic Ergothioneine Biosynthesis [J].

Cheng, Ronghai ;

Wu, Lian ;

Lai, Rui ;

Peng, Chao ;

Naowarojna, Nathchar ;

Hu, Weiyao ;

Li, Xinhao ;

Whelan, Stephen A. ;

Lee, Norman ;

Lopez, Juan ;

Zhao, Changming ;

Yong, Youhua ;

Xue, Jiahui ;

Jiang, Xuefeng ;

Grinstaff, Mark W. ;

Deng, Zixin ;

Chen, Jiesheng ;

Cui, Qiang ;

Zhou, Jiahai ;

Liu, Pinghua .

ACS CATALYSIS, 2020, 10 (16) :8981-8994

[10] Role of Ergothioneine in Microbial Physiology and Pathogenesis [J].

Cumming, Bridgette M. ;

Chinta, Krishna C. ;

Reddy, Vineel P. ;

Steyn, Adrie J. C. .

ANTIOXIDANTS & REDOX SIGNALING, 2018, 28 (06) :431-444

← 1 2 3 4 →