Benzylfumaric, benzylmaleic, and Z- and E-phenylitaconic acids: Synthesis, characterization, and correlation with a metabolite generated by Azoarcus tolulyticus tol-4 during anaerobic toluene degradation

Applied and Environmental Microbiology

Volumn 62, Issue 3, 1996, Pages 974-978

  Migaud, Marie E ^a   Chee Sanford, Joanne C ^b   Tiedje, James M ^a,b   Frost, J W ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUMARIC ACID DERIVATIVE; ITACONIC ACID; MALEIC ACID DERIVATIVE; TOLUENE;

ACIDIFICATION; ARTICLE; BACTERIAL METABOLISM; BIODEGRADATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

BENZYL COMPOUNDS; BENZYLIDENE COMPOUNDS; BIODEGRADATION, ENVIRONMENTAL; FUMARATES; GRAM-NEGATIVE FACULTATIVELY ANAEROBIC RODS; MALEATES; NITROGEN FIXATION; SUCCINATES; TOLUENE;

EID: 0030044301     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.62.3.974-978.1996     Document Type: Article

References (19)

1. Anders, H.-J., A. Kaetzke, P. Kämpfer, W. Ludgig, and G. Fuchs. 1995. Taxonomic position of aromatic-degrading denitrifying pseudomonad strains K172 and KB740 and their description as new members of the genera Thauera. as Thauera aromatica sp. nov., and Azoarcus, as Azoarcus evansii sp. nov., respectively, members of the beta subclass of the Proteobacteria, Int. J. Syst Bacteriol. 45:327-333.
2. Andersson, J., and L. Eberson. 1977 Cathodic reduction of derivatives of dibenzylidenesuccinic acid; attempted electrohydrocyclization of conjugated systems. Nouv. J. Chim. 1:413-418
3. Beller, H. R. 1995. Anaerobic metabolism of toluene and other aromatic compounds by sulfate-reducing soil bacteria. Ph.D. thesis. Stanford University, Stanford, Calif.
4. Beller, H. R., M. Reinhard, and D. Grbic-Galic. 1992. Metabolic by-products of anaerobic toluene degradation by sulfate-reducing enrichment cultures. Appl. Environ. Microbiol. 58:3192-3195.
5. Chee-Sanford, J. C., J. W. Frost, M. R. Fries, and J. M. Tiedje. 1996. Evidence for acetyl coenzyme A and cinnamoyl coenzyme A in the anaeiobic toluene mineralization pathway in Azoarcus toluliticus Tol-4. Appl. Environ. Microbiol. 62:964-973.
6. Cook, M. P., Jr. 1981. New ylide anions. A vinyl anion equivalent for substituted fumarate esters. Tetrahedron Lett. 22:381-384.
7. Cooper, J. W. 1980. Spectroscopic techniques for organic chemists, p. 278. John Wiley & Sons, New York.
8. Evans, P. J., W. Ling, B. Goldschmidt, E. R. Ritter, and L. Y. Young. 1992. Metabolites formed during anaerobic transformation of tokiene and o-xylene and their proposed relationship to the initial steps of toluene mineralization. Appl. Environ. Microbiol. 58:496-501.
9. Fries, M. R., J.-Z. Zhou, J. C. Chee-Sanford, and J. M. Tiedje. 1994 Isolation, characterization, and distribution of denitrifying toluene degraders from a variety of habitats. Appl. Environ. Microbiol. 60:2802-2810.
10. Gornowicz, G. A., and J. W. Ryan. 1966. Thionoacyloxysilanes. J. Org. Chem. 31:3439-3440
11. Horning, E. C., and G. N. Walker. 1952. Cyclizations of benzylsuccinic acids J. Am. Chem. Soc. 74:5147-5151.
12. Leitner, W., J. M. Brown, and H. Brunner. 1993 Mechanistic aspects of the rhodium-catalyzed enantioselective transfer hydrogenation of αβ-unsaturated carboxylic acids using formic acid/triethylamine (5:2) as the hydrogen source J. Am. Chem. Soc. 115:152-159
13. Momose, T., K.-I. Kanal, T. Nakamura, and Y. Kuni. 1977. Synthetic studies on lignans and related compounds V. Regiospecificity in the photocyclization of 2,3-dihenzylidenebutyrolactones. Chem. Pharm Bull. 25:2755-2760.
14. Montchamp, J.-L., and J. W. Frost. 1994 Synthesis and evaluation of 3-dehydroquinate synthase transition state analogues. J. Org. Chem. 59:7596-7601.
15. Nishiyama, H., M. Sasaki, and K. Itoh. 1981. Stereoselective addition of readily available organocopper reagents to dimethyl acetylenedicarboxylate. Chem. Lett 1981:905-908
16. Okada, T., and R. Okawara. 1972. The reaction of triphenylphosphine with some organometal haloacetates. J. Organometal Chem. 42:117-121.
17. Owens, J. D., and R. M. Keddie. 1969 The nitrogen nutrition of soil and herbage coryneform bacterium. J. Appl. Bacteriol 32:338-347.
18. Seyfried, B., G. Glod, R. Schocher, A. Tschech, and J. Zeyer. 1994 Initial reactions in the anaerobic oxidation of toluene and m-xylene by denitrifrying bacteria. Appl. Environ. Microbiol. 60:4047-4052.
19. Zhou, J.-Z., M. R. Fries, J. C. Chee-Sanford, and J. M. Tiedje. 1995 Phylogenetic analyses of a new group of denitrifiers capable of anaerobic growth on toluene, description of Azoarcus tolulyticus sp. nov. Int. J Syst. Bacteriol 45:500-506