Oxidation of polycyclic aromatic heterocycles by Pseudomonas fluorescens TTC1

Bianchi, Daniele; Bosetti, Aldo; Cidaria, D.; Bernardi, Antonella; Gagliardi, I.; D'Amico, Paul

doi:10.1007/s002530050979

Cited by 22 publications

(15 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The biotransformation ( P. putida UV4 whole cells, expressing TDO) of biphenylene 1 b had resulted in cis ‐dihydroxylation at a ring junction (angular) bond to give only cis ‐dihydrodiol 2 b . Conversely, the biotransformation of tricyclic heteroarenes 1 c–1 e by mutant strains of P. putida 9816/11 and P. fluorescens TTC1(NCIMB 40605), both expressing NDO, resulted in lateral cis ‐dihydroxylations to yield cis ‐diols 2 c–2 e –. Molecular docking studies were conducted to compare with these reported biotransformation results and to predict if similar results would be found using TDO with potential substrates 1 c–1 e .…”

Section: Resultsmentioning

confidence: 94%

Cis‐Dihydroxylation of Tricyclic Arenes and Heteroarenes Catalyzed by Toluene Dioxygenase: A Molecular Docking Study and Experimental Validation

et al. 2019

View full text Add to dashboard Cite

Molecular docking studies of toluene dioxygenase led to the prediction that angular and lateral cisdihydroxylation of tricyclic arene and heteroarene substrates could occur. Biotransformations of biphenylene, dibenzofuran, carbazole and dibenzothiophene, using Pseudomonas putida UV4 whole cells, expressing toluene dioxygenase, confirmed that both angular and lateral cis-dihydroxylation had occurred in the predicted regioselective and stereoselective manner. The toluene dioxygenase-catalysed (Pseudomonas putida UV4) biotransformation of dibenzofuran was optimized, to produce 1,2-dihydrodibenzofuran-1,2-diol as the major metabolite in excellent yield. 2-Hydroxydibenzofuran, resulting from dehydration of 1,2-dihydrodibenzofuran-1,2-diol, was also found to undergo cis-dihydroxylation to give a very minor cis-dihydrodiol metabolite. The enantiopurity (> 98% ee) and (1R,2S) absolute configuration of the major dibenzofuran cis -dihydrodiol was rigorously established by catalytic hydrogenation and formation of methoxy(trifluoromethyl)phenylacetate derivatives and by X-ray crystallography of an epoxide derivative. Biotransformation of carbazole yielded anthranilic acid as the major metabolite and was consistent with angular cis-dihydroxylation. Synthesis of a cis-diol epoxide derivative showed that the main cis-dihydrodiol metabolite of dibenzofuran has potential in the chemoenzymatic synthesis of natural products.

show abstract

Section: Resultsmentioning

confidence: 94%

Cis‐Dihydroxylation of Tricyclic Arenes and Heteroarenes Catalyzed by Toluene Dioxygenase: A Molecular Docking Study and Experimental Validation

et al. 2019

View full text Add to dashboard Cite

show abstract

“…6,7,[10][11][12][13][14][15][16][17][18][19] Conversely, cis-dihydrodiol metabolites, from polycyclic arenes or heteroarenes, are rarely used in chemoenzymatic synthesis. 20 Thus, although the isolation and stereochemical assignment of cis-dihydrodiols from tricyclic aromatic substrates was reported, using naphthalene dioxygenase (NDO) 21 or biphenyl dioxygenase (BPDO) [20][21][22][23] as biocatalysts, few examples of their employment as chiral synthons have been documented. Furthermore, biotransformations of polycyclic arene substrates, with the latter dioxygenase types, often resulted in the formation of mixtures of cis-dihydrodiol isomers in relatively low yields.…”

Section: Scheme 3 Synthesis Of Ribisin B Scheme 4 Attempted Synthesmentioning

confidence: 99%

Chemoenzymatic Synthesis of (−)-Ribisins A and B from Dibenzo[b,d]furan

et al. 2019

View full text Add to dashboard Cite

cis-Dihydrodiols, derived from monocyclic aromatic compounds, are valuable chiral pool intermediates for the synthesis of cyclic natural products. A drawback of this approach to the synthesis of polycyclic secondary metabolites, is that the additional rings must be annulated. To date, relatively few chiral natural products have been synthesized from polycyclic arene cis-dihydrodiols. Fungal metabolites ribisins A and B, have now be obtained by functional group manipulation of a major tricyclic arene metabolite, obtained from toluene dioxygenase-catalyzed regioselective and stereoselective cis-dihydroxylation of dibenzo[b,d]furan. The synthetic sequences were marginally shorter than the alternative routes using monocyclic arene cis-dihydrodiols and required no carbon-carbon bond-forming reaction.

show abstract

“…Акридин цис-1,2-дигидродиол (CI) был также получен в результате трансфрмации акридина (C) мутантным штаммом Pseudomonas fluorescens TTC1 (NCIMB 40605) [Bianchi et al, 1997].…”

Section: CIV Cvunclassified

Methods of Biotechnology in the Synthesis of Drugs (2nd Ed.)

Parshikov¹

2018

View full text Add to dashboard Cite

н. Калюжин О.В. к.б.н. Зарайский Е.И. Монография рекомендована для публикации Ученым советом Института прикладной механики Российской академии наук Паршиков И.А. Методы биотехнологии в синтезе лекарств.-2-е изд., перераб. и доп.-Даллас: Праймедиа Е-лаунч, 2018. −120 с. Монография посвящена методам биотехнологии. В работе описаны примеры применения микробных технологий для получения прозводных противомалярийных лекарств из ряда азотистых гетероциклов (азааренов, хинолонов, насыщенных азотистых гетероциклов) и терпеноидов. Предлагается поиск альтернативных путей синтеза веществ, которые трудно получить с помощью методов органическй химии. Микробные технологии синтеза органических соединений могут найти практическое применение в получении различных лекарственных средств.

show abstract

Oxidation of polycyclic aromatic heterocycles by Pseudomonas fluorescens TTC1

Cited by 22 publications

References 15 publications

Cis‐Dihydroxylation of Tricyclic Arenes and Heteroarenes Catalyzed by Toluene Dioxygenase: A Molecular Docking Study and Experimental Validation

Cis‐Dihydroxylation of Tricyclic Arenes and Heteroarenes Catalyzed by Toluene Dioxygenase: A Molecular Docking Study and Experimental Validation

Chemoenzymatic Synthesis of (−)-Ribisins A and B from Dibenzo[b,d]furan

Methods of Biotechnology in the Synthesis of Drugs (2nd Ed.)

Contact Info

Product

Resources

About