Bacterial scission of ether bonds.
نویسندگان
چکیده
INTRODUCTION .......................................................................................................................................................216 PROBLEM POLLUTANTS AND ETHER SCISSION..........................................................................................217 Agrochemicals..........................................................................................................................................................217 Polyethers.................................................................................................................................................................218 Polyethylene glycols ............................................................................................................................................218 Polypropylene glycols and polytetramethylene glycols ..................................................................................219 Detergents ................................................................................................................................................................219 Builder compounds.............................................................................................................................................219 Alcohol ethoxylates .............................................................................................................................................219 Alkylphenol ethoxylates......................................................................................................................................220 Alkylethoxy sulfate surfactants .........................................................................................................................220 BIOCHEMICAL MECHANISMS OF ETHER CLEAVAGE................................................................................221 Oxygenation .............................................................................................................................................................221 Oxidation by Cytochromes P-450 .........................................................................................................................221 Hydroxyl Shift Mechanisms ..................................................................................................................................223 Hydrolysis ................................................................................................................................................................225 Anaerobic O Dealkylation of Alkyl-Aryl Ethers .................................................................................................225 Oxidation to Carboxylic Acids ..............................................................................................................................226 Reduction .................................................................................................................................................................227 Carbon-Oxygen Bond Cleavage by Lyases ..........................................................................................................228 CONCLUDING REMARKS......................................................................................................................................228 State of Knowledge and Prospects .......................................................................................................................228 Pathways...............................................................................................................................................................228 Enzymes................................................................................................................................................................229 Emerging Themes ...................................................................................................................................................229 Natural Substrates for Ether Cleavage Systems ................................................................................................229 ACKNOWLEDGMENT..............................................................................................................................................230 REFERENCES ............................................................................................................................................................230
منابع مشابه
Reaction Pathways and Energetics of Etheric C−O Bond Cleavage Catalyzed by Lanthanide Triflates
Efficient and selective cleavage of etheric C−O bonds is crucial for converting biomass into platform chemicals and liquid transportation fuels. In this contribution, computational methods at the DFT B3LYP level of theory are employed to understand the efficacy of lanthanide triflate catalysts (Ln(OTf)3, Ln = La, Ce, Sm, Gd, Yb, and Lu) in cleaving etheric C−O bonds. In agreement with experimen...
متن کاملMechanistic details of acid-catalyzed reactions and their role in the selective synthesis of triptane and isobutane from dimethyl ether
We report here kinetic and isotopic evidence for the elementary steps involved in dimethyl ether (DME) homologation and for their role in the preferential synthesis of 2,2,3-trimethylbutane (triptane) and isobutane. Rates of methylation of alkenes and of hydrogen transfer, isomerization and b-scission reactions of the corresponding alkoxides formed along the homologation path to triptane were m...
متن کاملDirect detection of products from the pyrolysis of 2-phenethyl phenyl ether.
The pyrolysis of 2-phenethyl phenyl ether (PPE, C(6)H(5)C(2)H(4)OC(6)H(5)) in a hyperthermal nozzle (300-1350 °C) was studied to determine the importance of concerted and homolytic unimolecular decomposition pathways. Short residence times (<100 μs) and low concentrations in this reactor allowed the direct detection of the initial reaction products from thermolysis. Reactants, radicals, and mos...
متن کاملSynthesis of Zinc Dimethyldithiocarbamate by Reductive Disulfide Bond Cleavage of Tetramethylthiuram Disulfide in Presence of Zn2+
The zinc(II) complex [Zn2(dmdtc)2(μ-dmdtc)2] has been synthesized directly from thiram ligand, containing a disulfide bond {dmdtc = N,N-dimethyldithiocarbamate; thiram = N,N-tetramethylthiuram disulfide}, and characterized by elemental analysis and spectroscopic methods. Surprisingly thiram, undergoes a reductive disulfide bond scission upon reaction with Zn2+ in methanolic media to give the [Z...
متن کاملDioxygenolytic cleavage of aryl ether bonds: 1,2-dihydro-1,2-dihydroxy-4-carboxybenzophenone as evidence for initial 1,2-dioxygenation in 3- and 4-carboxy biphenyl ether degradation.
A bacterial strain, Pseudomonas sp. POB 310, was enriched with 4-carboxy biphenyl ether as sole source of carbon and energy. Resting cells of POB 310 co-oxidize a substrate analogue, 4-carboxybenzophenone, yielding 1,2-dihydro-1,2-dihydroxy-4-carboxy-benzophenone. The ether bond of 3- and 4-carboxy biphenyl ether is cleaved analogously by initial 1,2-dioxygenation, yielding a hemiacetal which i...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Microbiological reviews
دوره 60 1 شماره
صفحات -
تاریخ انتشار 1996