Benzylsuccinate

Figure 2-101. Supen mpositlon of a set of conformations of 2R-benzylsuccinate with the benzene ring fixed.

Thauera sp. strain DNT-1 is able to degrade toluene under aerobic conditions mediated by a dioxygenase, and under denitrifying conditions in the absence of oxygen by the anaerobic benzylsuccinate pathway (Shinoda et al. 2004). Whereas the tod genes were induced under aerobic conditions, the bss genes were induced under both aerobic and anaerobic conditions. 

It has been shown that pure cultures of bacteria under anaerobic denitrifying conditions may produce benzylsuccinate as a metabolite of toluene (Evans et al. 1992 Migaud et al. 1996 Beller et al. 1996). Demonstration of this and the corresponding methylbenzyl succinates from xylenes has been used to demonstrate metabolism of toluene and xylene in an anaerobic aquifer (Beller et al. 1995, 2002). 

Seller HR (2002) Analysis of benzylsuccinates in groundwater by liquid chromatography/tandem mass spectrometry and its use for monitoring in situ BTEX biodegradation. Environ Sci Technol 36 2724-2728. 

Reusser DE, JD Istok, HR Beller, JA Field (2002) In situ transformation of deuterated toluene and xylene to benzylsuccinic acid analogues in BTEX-contaminated aquifers. Environ Sci Technol 36 4127-4134. 

Krieger CJ, W Roseboom, SPJ Albracht, AM Sporman (2001) A stable organic free radical in anaerobic benzylsuccinate synthase of Azoarcus sp. strain T.J Biol Chem TIC. 12924-12927. 

Leuthner B, C Leutwein, H Schulz, P Horth, W Haehnel, E Schiltz, H Schagger, J Heider (1998) Biochemical and genetic characterisation of benzylsuccinate synthase from Thauera aromatica a new glycyl-radical catalysing the first step in anaerobic toluene degradation. Mol Microbiol 28 515-628. 

Verfiirth K, AJ Pierik, C Leutwein, S Zorn, 1 Heider (2004) Substrate specificities and electron paramagnetic resonance properties of benzylsuccinate synthesis in anaerobic toluene and m-xylene metabolism. Arch Microbiol 181 155-162. 

Beller HR, AM Spormann (1997b) Benzylsuccinate formation as a means of anaerobic toluene activation by sulfate-reducing strain PRTOLl. Appl Environ Microbiol 63 3729-3731. 

Beller HR, AM Spormann (1998) Analysis of the novel benzylsuccinate synthase reaction for anaerobic toluene activation based on structural studies of the product. J Bacteriol 180 5454-5457. 

Biegert T, G Fuchs, J Heider (1996) Evidence that anaerobic oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate. Eur J Biochem 238 661-668. 

Benzol hjthiophene, see Naphthalene 1,2,3-Benzotriazin-4 (3/J -one, see Azinnhos-methyl Benzotriazole, see Tetrachloroethylene Benzyl alcohol, see Benzo[a]anthracene, Benzyl butyl phthalate. Benzyl chloride, Permethrin. o-Xylene, m-Xylene, p-Xylene. Toluene 0-Benzyl alcohol, see o-Xylene m-Benzyl alcohol, see m-Xylene p-Benzyl alcohol, see p-Xylene 10-Benzyl-10-hydroanthracen-9-one, see Benzo [ a] anthracene Benzyl hydroperoxide, see Toluene Benzyl nitrate, see Toluene Benzylsuccinic acid, see Toluene... 

Reusser, D.E. and Field, J.A. Determination of benzylsuccinic acid in gasoline-contaminated groundwater by solid-phase extraction coupled with gas chromatography-mass spectrometry. J. Chromatogr. A, 953(l-2) 215-225. 2002. 

In the tricyclic inhibitor series amidation of benzhydryl ester 81b with phenyllactic acid or mono-ferf-butyl /i-benzylsuccinate gives 395 (92EPP481522) and 396 (95USP5455242), respectively. A similar amidation... 

Benzylsuccinic acid and derivs 2 B100 benzylsuccinyl diazide 2 B100... 

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