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Chemical Compound Review

Oxolane     oxolane

Synonyms: Furanidine, Hydrofuran, furanidinF, hydrofuraF, Agrisynth THF, ...
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Disease relevance of tetrahydrofuran


Psychiatry related information on tetrahydrofuran

  • 2,8-Dimethyl-1-oxa-8-azaspiro[4,5]decan-3-one (17), designed by incorporating the tetrahydrofuran ring moiety of muscarone into an 8-azaspiro[4,5]decane skeleton, and related 1-oxa-8-azaspiro[4.5]decanes were synthesized and assessed as M1 muscarinic agonists for the symptomatic treatment of dementia of Alzheimer's type [6].

High impact information on tetrahydrofuran

  • Discovery of lipid peroxidation products formed in vivo with a substituted tetrahydrofuran ring (isofurans) that are favored by increased oxygen tension [7].
  • This PCNA-dependent system repaired natural AP sites as well as tetrahydrofuran residues [8].
  • Tetrahydrofuran residues are efficiently repaired in a Xenopus laevis oocyte extract in which most repair events involve ATP-dependent incorporation of no more than four nucleotides (Y. Matsumoto and D. F. Bogenhagen, Mol. Cell. Biol. 9:3750-3757, 1989; Y. Matsumoto and D. F. Bogenhagen, Mol. Cell. Biol. 11:4441-4447, 1991) [8].
  • (+-)-2-[Hydroxy[tetrahydro-2-(octadecyloxy)methylfuran-2- yl]methoxyl]phosphinyloxy-N,N,N-trimethylethaniminium hydroxide, inner salt (SRI 62-834) is a tetrahydrofuran analogue of platelet activating factor (PAF) that is currently entering clinical trial [9].
  • In model studies it is shown that the first-order rate constant for decarboxylation can indeed exceed 50 s(-1) in tetrahydrofuran as solvent, approximately 10(3) times faster than achieved in previous model systems [10].

Chemical compound and disease context of tetrahydrofuran


Biological context of tetrahydrofuran

  • By comparing the interaction of DNA glycosylases with PYR and the structurally related tetrahydrofuran abasic site analog, we assess the importance of the positively charged ammonium group of the pyrrolidine in binding to the active site of these enzymes [16].
  • The utility of oxidative cyclization reactions for the construction of tetrahydrofuran rings has been examined [17].
  • The consensus sequence for efficient bypass of tetrahydrofuran was over-represented in several frames relative to the lesion [3].
  • Asymmetric enzyme-catalyzed hydrolysis of methylene-interrupted bis-epoxides 1 a and 1 b catalyzed by bacterial epoxide hydrolases furnished tetrahydrofuran derivatives 2 a and 2 b through a hydrolysis-rearrangement cascade [18].
  • Both acetylation and deoxygenation of either or both of two OH groups adjacent to the tetrahydrofuran (THF) rings resulted in a significant decrease in inhibitory potency [19].

Anatomical context of tetrahydrofuran

  • When delivered using tetrahydrofuran as a novel solvent, all carotenoids were absorbed by cultured cells [20].
  • Selective extraction, solubilization, and reversed-phase high-performance liquid chromatography separation of the main proteins from myelin using tetrahydrofuran/water mixtures [21].
  • Mucoxin, an annonaceous acetogenin isolated from bioactive leaf extracts of Rollinia mucosa, is the first acetogenin containing a hydroxylated trisubstituted tetrahydrofuran (THF) ring [22].
  • In this work, the polydimethyl-methylhydrosiloxane and polydimethyl-methylethylenesilosiane, as a substrate, were blended with cholesteryl oleyl carbonate (COC) in tetrahydrofuran, and then crosslinked into membranes on glass plates by means of the platinum catalyst at 110 degrees C for 20 min [23].
  • The plasmas were examined for conjugates of radioactive phenolic steroids by recovery on columns of Amberlite XAD-2 or by extraction with tetrahydrofuran followed by chromatography on a column of DEAE-Sephadex A-25 in a gradient of NaCl [24].

Associations of tetrahydrofuran with other chemical compounds

  • APE1 showed a similar K(m) value for matched, 3' mispaired, or nucleoside analog beta-l-dioxolane-cytidine terminated nicked DNA as well as for DNA containing a tetrahydrofuran, an abasic site analog [25].
  • Redox potentials of a number of triphenyl- or tributyl-substituted Si-, Ge-, or Sn-centered radicals, R(3)M(*), have been measured in acetonitrile, tetrahydrofuran, or dimethyl sulfoxide by photomodulated voltammetry or through a study of the oxidation process of the corresponding anions in linear sweep voltammetry [26].
  • Hydroxyl-directed 1,4-reduction of this functionality in 25 with LiAlH(4)/CuI/hexamethylphosphoramide/tetrahydrofuran sets the stage for the implementation of a Grob fragmentation and expedited generation of 27 [27].
  • Using tetrahydrofuran (THF) and 0.1% glacial acetic acid (HOAc) in an H(2)O/acetonitrile (ACN) mobile phase greatly increased the resolution and retention reproducibility of lipid radical adducts in LC/ESR [28].
  • We report here that while Ape1 incision of the AP site analog tetrahydrofuran (F-DNA) was approximately 7300-fold reduced in 4 mM EDTA relative to Mg2+, cleavage of ethane (E-DNA) and propane (P-DNA) acyclic abasic site analogs was only 20 and 30-fold lower, respectively, in EDTA compared to Mg2+ [29].

Gene context of tetrahydrofuran

  • However once the THF residue was displaced at least a single nucleotide, stimulation of FEN1 activity by APE1 resumes [30].
  • In our conditions, five metabolites were formed in vitro and subsequently analyzed by liquid chromatography-mass spectrometry; P450-dependent oxidations occurred either on the tetrahydrofuran ring (M3 and M4), the aniline ring (M5), and the aliphatic chain (M2) or resulted from the N-dealkylation and loss of the tetrahydrofuran ring (M1) [31].
  • The effects of ethanol, methanol, tetrahydrofuran, acetonitrile, acetone and dimethylsulfoxide on microsomal epoxide hydrolase depended on the substrate tested, whereas both cytosolic enzymes were not at all, or only slightly, affected by these solvents [32].
  • We confirmed this mechanism for the DNA polymerase alpha holoenzyme purified from Drosophila melanogaster embryos and studied the interaction of Drosophila pol alpha with synthetic oligonucleotide template-primers containing modified tetrahydrofuran moieties as model abasic lesions chemically engineered at a number of defined sites [33].
  • Experiments using tetrahydrofuran or alpha-deoxyadenosine-containing substrates indicate that the activity induced at low pH may be similar to the activity of exonuclease III from E. coli [34].

Analytical, diagnostic and therapeutic context of tetrahydrofuran

  • A gel mobility shift assay was used to assay binding of Fpg protein to a noncleavable substrate analog, namely an oligodeoxynucleotide duplex containing a single tetrahydrofuran residue [35].
  • Hydrogen/deuterium isotopic substitution neutron diffraction techniques have been used to measure the structural correlation functions of liquid tetrahydrofuran at room temperature [36].
  • Their base strengths are established in tetrahydrofuran (THF) solution by means of spectrophotometric titration and compared with those of eight reference superbases designed specially for this study, P2- and P4-iminophosphoranes [37].
  • Relevant physicochemical data of the porous structure (specific surface area (sigma), pore volume (Vp), volume fraction of pores (epsilon(p)), and intermicroglobule volume (epsilon(z))) of the monolithic columns were determined by inverse size exclusion chromatography in tetrahydrofuran [38].
  • Segregation effects were observed when the azeotrope mixture was diluted with tetrahydrofuran, resulting in large molar mass distribution discrimination effects in the MALDI spectra [39].


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  14. Kinetics of 1,4-dioxane biodegradation by monooxygenase-expressing bacteria. Mahendra, S., Alvarez-Cohen, L. Environ. Sci. Technol. (2006) [Pubmed]
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  17. Oxidative cyclization based on reversing the polarity of enol ethers and ketene dithioacetals. Construction of a tetrahydrofuran ring and application to the synthesis of (+)-nemorensic Acid. Liu, B., Duan, S., Sutterer, A.C., Moeller, K.D. J. Am. Chem. Soc. (2002) [Pubmed]
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  19. Synthesis and inhibitory action of novel acetogenin mimics with bovine heart mitochondrial complex I. Hamada, T., Ichimaru, N., Abe, M., Fujita, D., Kenmochi, A., Nishioka, T., Zwicker, K., Brandt, U., Miyoshi, H. Biochemistry (2004) [Pubmed]
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  21. Selective extraction, solubilization, and reversed-phase high-performance liquid chromatography separation of the main proteins from myelin using tetrahydrofuran/water mixtures. Díaz, R.S., Regueiro, P., Monreal, J., Tandler, C.J. J. Neurosci. Res. (1991) [Pubmed]
  22. Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies. Narayan, R.S., Borhan, B. J. Org. Chem. (2006) [Pubmed]
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