دورية أكاديمية
أعرض في EDS

Allyl Aryl Ether Cleavage by Blautia sp. MRG-PMF1 Cocorrinoid O -Demethylase.

التفاصيل البيبلوغرافية
العنوان: Allyl Aryl Ether Cleavage by Blautia sp. MRG-PMF1 Cocorrinoid O -Demethylase.
المؤلفون: Mi HTN; Metalloenzyme Research Group and Department of Plant Science and Technology, Chung-Ang Universitygrid.254224.7, Anseong, Republic of Korea., Chaiyasarn S; Metalloenzyme Research Group and Department of Plant Science and Technology, Chung-Ang Universitygrid.254224.7, Anseong, Republic of Korea., Eser BE; Department of Engineering, Aarhus Universitygrid.7048.b, Aarhus, Denmark., Tan SRS; Metalloenzyme Research Group and Department of Plant Science and Technology, Chung-Ang Universitygrid.254224.7, Anseong, Republic of Korea., Burapan S; Metalloenzyme Research Group and Department of Plant Science and Technology, Chung-Ang Universitygrid.254224.7, Anseong, Republic of Korea., Han J; Metalloenzyme Research Group and Department of Plant Science and Technology, Chung-Ang Universitygrid.254224.7, Anseong, Republic of Korea.
المصدر: Microbiology spectrum [Microbiol Spectr] 2022 Oct 26; Vol. 10 (5), pp. e0330522. Date of Electronic Publication: 2022 Oct 05.
نوع المنشور: Journal Article; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: ASM Press Country of Publication: United States NLM ID: 101634614 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 2165-0497 (Electronic) Linking ISSN: 21650497 NLM ISO Abbreviation: Microbiol Spectr Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Washington, DC : ASM Press, 2013-
مواضيع طبية MeSH: Methyl Ethers* , Environmental Pollutants*, Ether ; Oxidoreductases, O-Demethylating ; Naphthols ; Ethers/chemistry ; Ethers/metabolism ; Ethyl Ethers ; Vitamin B 12 ; Biocompatible Materials
مستخلص: Coabalamin-dependent O -demethylase in Blautia sp. strain MRG-PMF1 was found to catalyze the unprecedented allyl aryl ether cleavage reaction. To expand the potential biotechnological applications, the reaction mechanism of the allyl aryl ether C-O bond cleavage, proposed to utilize the reactive Co(I) supernucleophile species, was studied further from the anaerobic whole-cell biotransformation. Various allyl naphthyl ether derivatives were reacted with Blautia sp. MRG-PMF1 O -demethylase, and stereoisomers of allyl naphthyl ethers, including prenyl and but-2-enyl naphthyl ethers, were converted to the corresponding naphthol in a stereoselective manner. The allyl aryl ether cleavage reaction was regioselective, and 2-naphthyl ethers were converted faster than the corresponding 1-naphthyl ethers. However, MRG-PMF1 cocorrinoid O -demethylase was not able to convert (2-methylallyl) naphthyl ether substrates, and the conversion of propargyl naphthyl ether was extremely slow. From the results, it was proposed that the allyl ether cleavage reaction follows the nucleophilic conjugate substitution (S N 2') mechanism. The reactivity and mechanism of the new allyl ether cleavage reaction by cobalamin-dependent O -demethylase would facilitate the application of Blautia sp. MRG-PMF1 O -demethylase in the area of green biotechnology. IMPORTANCE Biodegradation of environmental pollutants and valorization of biomaterials in a greener way is of great interest. Cobalamin-dependent O -demethylase in Blautia sp. MRG-PMF1 exclusively involves anaerobic C1 metabolism by cleaving the C-O bond of aromatic methoxy group and also produces various aryl alcohols by metabolizing allyl aryl ether compounds. Whereas methyl ether cleavage reaction is known to follow the S N 2' mechanism, the reaction pattern and mechanism of the new allyl ether cleavage reaction by cobalamin-dependent O -demethylase have never been studied. For the first time, stereoselectivity and the S N 2' mechanism of allyl aryl ether cleavage reaction by Blautia sp. MRG-PMF1 O -demethylase is reported, and the results would facilitate the application of Blautia sp. MRG-PMF1 O -demethylase in the area of green biotechnology.
References: Enzyme Microb Technol. 2021 Jun;147:109780. (PMID: 33992403)
J Biol Chem. 2020 Aug 21;295(34):11971-11981. (PMID: 32571881)
J Am Chem Soc. 1969 Jun 4;91(12):3341-50. (PMID: 5791925)
Chem Rev. 2018 Jan 24;118(2):614-678. (PMID: 29337543)
Molecules. 2016 Aug 31;21(9):. (PMID: 27589718)
Org Lett. 2017 May 19;19(10):2670-2673. (PMID: 28453294)
J Agric Food Chem. 2014 Dec 24;62(51):12377-83. (PMID: 25437273)
J Bacteriol. 2012 Jul;194(13):3317-26. (PMID: 22522902)
ACS Omega. 2020 Nov 17;5(47):30696-30703. (PMID: 33283118)
J Agric Food Chem. 2017 Apr 26;65(16):3305-3310. (PMID: 28401758)
Acta Crystallogr D Biol Crystallogr. 2013 Aug;69(Pt 8):1609-16. (PMID: 23897483)
Proc Natl Acad Sci U S A. 2014 Oct 28;111(43):E4668-76. (PMID: 25313086)
Environ Microbiol. 2007 Oct;9(10):2512-21. (PMID: 17803776)
J Agric Food Chem. 2017 Mar 1;65(8):1620-1629. (PMID: 28211698)
Metabolites. 2019 Jul 10;9(7):. (PMID: 31295867)
Vitam Horm. 2008;79:293-324. (PMID: 18804699)
Eur J Nutr. 2019 Nov;58(Suppl 2):21-36. (PMID: 31642982)
Trends Biotechnol. 2015 Jul;33(7):371-3. (PMID: 25887333)
ACS Catal. 2019 May 3;9(5):3900-3905. (PMID: 31080689)
J Bacteriol. 2001 Jun;183(11):3276-81. (PMID: 11344134)
Org Lett. 2007 Mar 1;9(5):773-6. (PMID: 17284041)
Proc Natl Acad Sci U S A. 2019 Jul 9;116(28):13970-13976. (PMID: 31235604)
Proc Natl Acad Sci U S A. 2020 Jan 21;117(3):1395-1403. (PMID: 31848239)
ACS Catal. 2020 Sep 18;10(18):10375-10380. (PMID: 32974079)
Nat Commun. 2018 Jun 27;9(1):2487. (PMID: 29950589)
Proc Natl Acad Sci U S A. 2016 Oct 4;113(40):E5802-E5811. (PMID: 27634497)
J Bacteriol. 2019 May 22;201(12):. (PMID: 30936368)
فهرسة مساهمة: Keywords: Blautia sp. MRG-PMF1; O-demethylase; SN2′ reaction; allyl aryl ether cleavage; biotransformation; cocorrinoid; mechanism
المشرفين على المادة: 0F5N573A2Y (Ether)
EC 1.- (Oxidoreductases, O-Demethylating)
0 (Naphthols)
0 (propargyl ether)
0 (Ethers)
0 (Ethyl Ethers)
P6YC3EG204 (Vitamin B 12)
0 (Methyl Ethers)
0 (Environmental Pollutants)
0 (Biocompatible Materials)
تواريخ الأحداث: Date Created: 20221005 Date Completed: 20221028 Latest Revision: 20230103
رمز التحديث: 20240628
مُعرف محوري في PubMed: PMC9602652
DOI: 10.1128/spectrum.03305-22
PMID: 36197289
قاعدة البيانات: MEDLINE
الوصف
تدمد:2165-0497
DOI:10.1128/spectrum.03305-22