関: alkanesulfonic acid

English Journal

Steady-state kinetic isotope effects support a complex role of arg226 in the proposed desulfonation mechanism of alkanesulfonate monooxygenase.

Robbins JM1, Ellis HR.Author information 1Department of Chemistry and Biochemistry, Auburn University , Auburn, Alabama 36849, United States.AbstractThe alkanesulfonate monooxygenase system catalyzes the desulfonation of alkanesulfonates through proposed acid-base mechanistic steps that involves the abstraction of a proton from the alkane peroxyflavin intermediate and protonation of the FMN-O(-) intermediate. Both solvent and kinetic isotope studies were performed to define the proton transfer steps involved in the SsuD reaction. Substitution of the protium at the C1 position of octanesulfonate with deuterium resulted in an observed primary isotope effect of 3.0 ± 0.2 on the kcat parameter, supporting abstraction of the α-proton from the alkane peroxyflavin as the rate-limiting step in catalysis. Previous studies implicated Arg226 as the acid involved in the reprotonation of the hydroxyflavin intermediate. Solvent isotope kinetic studies gave an inverse isotope effect on (D2O)kcat of 0.75 ± 0.04 with no observable effect on (D2O)kcat/Km. This resulted in equivalent solvent isotope effects on (D2O)kcat and (D2O)(kcat)D, suggesting a solvent equilibrium isotope effect on a step occurring after the first irreversible step through product release. Data from proton inventory studies on kcat were best fit to a dome-shaped curve consistent with a conformational change to an open conformation during product release. The solvent isotope effect data coupled with the corresponding proton inventory results support and extend our previous observations that Arg226 donates a proton to the FMN-O(-) intermediate, triggering a conformational change that opens the enzyme to solvation and promotes product release.
Biochemistry.Biochemistry.2014 Jan 14;53(1):161-8. doi: 10.1021/bi401234e. Epub 2013 Dec 20.
The alkanesulfonate monooxygenase system catalyzes the desulfonation of alkanesulfonates through proposed acid-base mechanistic steps that involves the abstraction of a proton from the alkane peroxyflavin intermediate and protonation of the FMN-O(-) intermediate. Both solvent and kinetic isotope stu
PMID 24321058

Genomic and proteomic characterization of Gordonia sp. NB4-1Y in relation to 6 : 2 fluorotelomer sulfonate biodegradation.

Van Hamme JD1, Bottos EM, Bilbey NJ, Brewer SE.Author information 1Department of Biological Sciences, Thompson Rivers University, Kamloops, British Columbia, Canada V2C 0C8.AbstractGordonia sp. strain NB4-1Y was isolated from vermicompost using bis-(3-pentafluorophenylpropyl)-sulfide as the sole added sulfur source and was found to have a broad capacity for metabolizing organosulfur compounds. NB4-1Y is closely related to G. desulfuricans and was found to metabolize 6 : 2 fluorotelomer sulfonate (6 : 2 FTS) to 5 : 3 fluorotelomer acid (5 : 3 acid) via 6 : 2 fluorotelomer acid (6 : 2 FTCA), 6 : 2 unsaturated fluorotelomer acid (6 : 2 FTUCA) and 5 : 3 unsaturated fluorotelomer acid (5 : 3 Uacid). Given that the molecular and biochemical basis for the microbial metabolism of poly- and per-fluorinated compounds has yet to be examined, we undertook to investigate 6 : 2 FTS metabolism in NB4-1Y. To this end, a whole-genome shotgun sequence was prepared and two-dimensional differential in-gel electrophoresis was used to compare proteomes of MgSO4- and 6 : 2 FTS-grown cells. Of the three putative alkanesulfonate monooxygenases, four nitrilotriacetate monooxygenases and one taurine dioxygenase located in the draft genome, two nitrilotriacetate monooxygenases were differentially expressed in the presence of 6 : 2 FTS. It is hypothesized that these two enzymes may be responsible for 6 : 2 FTS desulfonation. In addition, a differentially expressed putative double bond reductase may be involved in the reduction of 5 : 3 Uacid to 5 : 3 acid. Other proteins differentially expressed during 6 : 2 FTS metabolism included a sulfate ABC transporter ATP-binding protein and two alkyl hydroperoxide reductases. This work establishes a foundation for future studies on the molecular biology and biochemistry of poly- and per-fluorinated compound metabolism in bacteria.
Microbiology (Reading, England).Microbiology.2013 Aug;159(Pt 8):1618-28. doi: 10.1099/mic.0.068932-0. Epub 2013 Jun 6.
Gordonia sp. strain NB4-1Y was isolated from vermicompost using bis-(3-pentafluorophenylpropyl)-sulfide as the sole added sulfur source and was found to have a broad capacity for metabolizing organosulfur compounds. NB4-1Y is closely related to G. desulfuricans and was found to metabolize 6 : 2
PMID 23744905

Bioinspired multiple-interaction model revealed in adsorption of low-density lipoprotein to surface containing saccharide and alkanesulfonate.

Li J1, Huang XJ, Vienken J, Xu ZK, Groth T.Author information 1MOE Key Laboratory of Macromolecular Synthesis and Functionalization (Ministry of Education), Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China.AbstractA new "multiple-interaction model" for low-density lipoprotein (LDL) adsorption to a specific surface containing saccharide and alkanesulfonate ligands is proposed. The model suggests that there are interactions of the saccharide component beyond electrostatic interactions of the alkanesulfonate component that both influence the LDL adsorption process. This concept of multiple interactions between saccharide and LDL was inspired by the similarity in structures of LDL receptors (LDLR), heparin, and heparans used in LDL-apheresis. The model was confirmed by SPR analysis by the adsorption maxima on SAM surfaces with different compositions of saccharide and alkanesulfonate and additionally by CD detection of the conformation of LDL when in contact with saccharide.
Langmuir : the ACS journal of surfaces and colloids.Langmuir.2013 Jul 2;29(26):8363-9. doi: 10.1021/la401464a. Epub 2013 Jun 21.
A new "multiple-interaction model" for low-density lipoprotein (LDL) adsorption to a specific surface containing saccharide and alkanesulfonate ligands is proposed. The model suggests that there are interactions of the saccharide component beyond electrostatic interactions of the alkanesulfonate com
PMID 23742692

Japanese Journal

Inclusion Complexes of Cyclodextrins with Benzo[c]cinnoline, Phenanthridine, and Phenanthrene in Aqueous Solution Containing an Organic Ion Having a Long Alkyl Chain

Hamai Sanyo
Bulletin of the Chemical Society of Japan 84(3), 290-297, 2011
… The 1:1 inclusion complexes further associate with an alkyltrimethylammonium cation (alkyl sulfate or alkanesulfonate) to form a 1:1:1 γ-CD–phenanthrene analog–alkyltrimethylammonium cation (alkyl sulfate or alkanesulfonate) inclusion complex. … The K2 value of the phenanthrene analog is increased with the alkyl chain length of the alkyltrimethylammonium cation (alkyl sulfate or alkanesulfonate). …
NAID 130004152886

Design of Alkanesulfonate Ionic Liquids for Lubricants

Itoh Toshiyuki,Watanabe Naoko,Inada Kento,Ishioka Akihiko,Hayase Shuichi,Kawatsura Motoi,Minami Ichiro,Mori Shigeyuki
Chemistry Letters 38(1), 64-65, 2009
Tribological properties of alkyl sulfate ionic liquids have been evaluated; hydrophobicity of ionic liquids significantly influenced the tribological characteristics and combination of phosphonium cat …
NAID 130004425346

ソルボリシスイオン化におよぼす脱離基の疎水効果と立体効果

前田大輔,松崎雅弘,清水宣次郎
基礎有機化学討論会要旨集（基礎有機化学連合討論会予稿集） 16(0), 2089-2089, 2002
… Rates of solvolysis have been measured for 1-adamantyl-X substrates, where X is a series of sterically hindered arene- or alkanesulfonate leaving groups, 1b-1d and 2b-2c. …
NAID 130004644777