Mechanistic Study of a Ru-Xantphos Catalyst for Tandem Alcohol Dehydrogenation and Reductive Aryl-Ether Cleavage

ACS Catalysis ◽  
2013 ◽  
Vol 3 (5) ◽  
pp. 963-974 ◽  
Author(s):  
Stephen C. Chmely ◽  
Seonah Kim ◽  
Peter N. Ciesielski ◽  
Gonzalo Jiménez-Osés ◽  
Robert S. Paton ◽  
...  
Keyword(s):  
Mechanistic Study ◽  
Aryl Ether ◽  
Ether Cleavage ◽  
Alcohol Dehydrogenation

scholarly journals Structural and Biochemical Characterization of the Early and Late Enzymes in the Lignin β-Aryl Ether Cleavage Pathway fromSphingobiumsp. SYK-6

2016 ◽  
Vol 291 (19) ◽  
pp. 10228-10238 ◽  
Author(s):  
Jose Henrique Pereira ◽  
Richard A. Heins ◽  
Daniel L. Gall ◽  
Ryan P. McAndrew ◽  
Kai Deng ◽  
...  
Keyword(s):  
Biochemical Characterization ◽  
Aryl Ether ◽  
Ether Cleavage

scholarly journals Roles of two glutathione S-transferases in the final step of the β-aryl ether cleavage pathway in Sphingobium sp. strain SYK-6

2020 ◽  
Author(s):  
Yudai Higuchi ◽  
Daisuke Sato ◽  
Naofumi Kamimura ◽  
Eiji Masai
Keyword(s):  
Aromatic Compounds ◽  
Specific Activity ◽  
Value Added ◽  
Degradation Process ◽  
Lignin Biodegradation ◽  
Aryl Ether ◽  
Ether Linkage ◽  
Ether Cleavage ◽  
Subsequent Degradation ◽  
Glutathione S Transferases

ABSTRACTSphingobium sp. strain SYK-6 is an alphaproteobacterial degrader of lignin-derived aromatic compounds, which can degrade all the stereoisomers of β-aryl ether-type compounds. SYK-6 cells convert four stereoisomers of guaiacylglycerol-β-guaiacyl ether (GGE) into two enantiomers of α-(2-methoxyphenoxy)-β-hydroxypropiovanillone (MPHPV) through GGE α-carbon atom oxidation by stereoselective Cα-dehydrogenases encoded by ligD, ligL, and ligN. The ether linkages of the resulting MPHPV enantiomers are cleaved by stereoselective glutathione S-transferases (GSTs) encoded by ligF, ligE, and ligP, generating (βRβS)-α-glutathionyl-β-hydroxypropiovanillone (GS-HPV) and guaiacol. To date, it has been shown that the gene products of ligG and SLG_04120 (ligQ), both encoding GST, catalyze glutathione removal from (βRβS)-GS-HPV, forming achiral β-hydroxypropiovanillone. In this study, we characterized the enzyme properties of LigG and LigQ and elucidated their roles in β-aryl ether catabolism. Purified LigG showed an approximately 300-fold higher specific activity for (βR)-GS-HPV than that for (βS)-GS-HPV, whereas purified LigQ showed an approximately six-fold higher specific activity for (βS)-GS-HPV than that for (βR)-GS-HPV. Analyses of mutants of ligG, ligQ, and both genes revealed that SYK-6 converted (βR)-GS-HPV using both LigG and LigQ, whereas only LigQ was involved in converting (βS)-GS-HPV. Furthermore, the disruption of both ligG and ligQ was observed to lead to the loss of the capability of SYK-6 to convert MPHPV. This suggests that GSH removal from GS-HPV catalyzed by LigG and LigQ, is essential for cellular GSH recycling during β-aryl ether catabolism.IMPORTANCEThe β-aryl ether linkage is most abundant in lignin, comprising 45%–62% of all intermonomer linkages in lignin; thus, cleavage of the β-aryl ether linkage together with the subsequent degradation process is considered the essential step in lignin biodegradation. The enzyme genes for β-aryl ether cleavage are useful for decomposing high-molecular-weight lignin, converting lignin-derived aromatic compounds into value-added products, and modifying lignin structures in plants to reduce lignin recalcitrance. In this study, we uncovered the roles of the two glutathione S-transferase genes, ligG and ligQ, in the conversion of GS-HPV isomers, which are generated in the β-aryl ether cleavage pathway in SYK-6. Adding our current results to previous findings allowed us to have a whole picture of the β-aryl ether cleavage system in SYK-6.

scholarly journals Data-Driven Advancement of Homogeneous Nickel Catalyst Activity for Aryl Ether Cleavage

ACS Catalysis ◽  
2020 ◽  
Vol 10 (13) ◽  
pp. 7021-7031 ◽  
Author(s):  
Manuel Cordova ◽  
Matthew D. Wodrich ◽  
Benjamin Meyer ◽  
Boodsarin Sawatlon ◽  
Clémence Corminboeuf
Keyword(s):  
Nickel Catalyst ◽  
Catalyst Activity ◽  
Data Driven ◽  
Aryl Ether ◽  
Ether Cleavage

Methyl aryl ether cleavage in benzazole syntheses in polyphosphoric acid

1970 ◽  
Vol 35 (9) ◽  
pp. 3147-3149 ◽  
Author(s):  
Charles M. Orlando ◽  
J. G. Wirth ◽  
D. R. Heath
Keyword(s):  
Polyphosphoric Acid ◽  
Aryl Ether ◽  
Ether Cleavage

scholarly journals Mechanistic Study on the Antibacterial Activity of Self-Assembled Poly(aryl ether)-Based Amphiphilic Dendrimers

2019 ◽  
Vol 2 (8) ◽  
pp. 3212-3224 ◽  
Author(s):  
Ramya Kannan ◽  
Palani Prabakaran ◽  
Ruchira Basu ◽  
Chinmai Pindi ◽  
Sanjib Senapati ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Mechanistic Study ◽  
Aryl Ether ◽  
Amphiphilic Dendrimers ◽  
Self Assembled
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