Aromatization microbial

Gonthier, M.P., Cheynier, V., Donovan, J.L., Manach, C., Morand, C., Mila, I., Lapierre, C., Remesy, C., and Scalbert, A., Microbial aromatic acid metabolites formed in the gut account for a major fraction of the polyphenols excreted in urine of rats fed red wine polyphenols, J. Nutr., 133, 461, 2003. 

Other examples of M.c. are anthranilate synthase and tryptophan synthase, which are involved in microbial Aromatic biosynthesis (see), and citrate lyase. The definition of M. c. may be extended to include the membrane-bound respiratory chain, the contractile protein complexes of muscle, and the ribosome (which also contains RNA), etc. 

Graham, T.L., A rapid high-resolution high performance hquid chromatography profiling procedure for plant and microbial aromatic secondary metabohtes. Plant Physiol., 95, 584-593, 1991a. 

Experimental procedures have been described in which the desired reactions have been carried out either by whole microbial cells or by enzymes (1—3). These involve carbohydrates (qv) (4,5) steroids (qv), sterols, and bile acids (6—11) nonsteroid cycHc compounds (12) ahcycHc and alkane hydroxylations (13—16) alkaloids (7,17,18) various pharmaceuticals (qv) (19—21), including antibiotics (19—24) and miscellaneous natural products (25—27). Reviews of the microbial oxidation of aUphatic and aromatic hydrocarbons (qv) (28), monoterpenes (29,30), pesticides (qv) (31,32), lignin (qv) (33,34), flavors and fragrances (35), and other organic molecules (8,12,36,37) have been pubflshed (see Enzyp applications, industrial Enzyt s in organic synthesis Elavors AND spices). 

Novel aromatic carboxylation reactions have been observed in the anaerobic transformation of phenols to ben2oates (82). A mixed anaerobic microbial consortium apparentiy transforms phenol (33) through an intermediate to ben2oic acid (34) via dehydroxylation. This reaction has not yet been widely exploited for its obvious synthetic value. 

G. S. Sayler, Microbial Decomposition of Chlorinated Aromatic Compounds, USEPA 600/2-86/090, Washington, D.C., 1986. 

W. C. Evans, Microbial Transformations of Aromatic Compounds, in D. Perlman, Fermentation Advances, S. 

Recently, XAD was used as material to control the stereochemical course of microbial reductions [19], In the presence of XAD, simple aliphatic and aromatic ketones were reduced to the corresponding (S)-alcohols in excellent enantioselec-tivity while low enantioselectivities were observed in the absence of the polymer (Figure 8.23). 

Enzyme preparations from liver or microbial sources were reported to show rather high substrate specificity [76] for the natural phosphorylated acceptor d-(18) but, at much reduced reaction rates, offer a rather broad substrate tolerance for polar, short-chain aldehydes [77-79]. Simple aliphatic or aromatic aldehydes are not converted. Therefore, the aldolase from Escherichia coli has been mutated for improved acceptance of nonphosphorylated and enantiomeric substrates toward facilitated enzymatic syntheses ofboth d- and t-sugars [80,81]. High stereoselectivity of the wild-type enzyme has been utilized in the preparation of compounds (23) / (24) and in a two-step enzymatic synthesis of (22), the N-terminal amino acid portion of nikkomycin antibiotics (Figure 10.12) [82]. 

Microbial cells may be subjected to stress from a number of sources in their environment. These include antibiotics, metal cations and metalloid oxyanions, aromatic hydrocarbons, chlorophenols,... 

Herbes SE, LR Schwall (1978) Microbial transformation of polycyclic aromatic hydrocarbons in pristine and petroleum-contaminated sediments. Appl Environ Microbiol 35 306-316. 

Klecka GM, WJ Maier (1988) Kinetics of microbial growth on mixtures of pentachlorophenol and chlorinated aromatic compounds. Biotechnol Bioeng 31 328-335. 

Harper DB (1977) Microbial metabolism of aromatic nitriles. Enzymology of C-N cleavage by Nocardia sp. (Rhodochrous group) NCIB 11216. Biochem J 165 309-319. 

Gibson DT, V Subramanian (1984) Microbial degradation of aromatic hydrocarbons. In Microbial degradation of organic compounds (Ed DT Gibson), pp. 181-252. Marcel Dekker Inc, New York. 

Hopper DJ (1978) Microbial degradation of aromatic hydrocarbons. In Developments in biodegradation of hydrocarbons-1 (Ed RJ Watkinson), pp. 85-112. Applied Science Publishers Ltd, London. 

Smith MR (1994) The physiology of aromatic hydrocarbon degrading bacteria. In Biochemistry of Microbial Degradation (Ed C Ratledge), pp. 347-378. Kluwer Academic Publishers, Dordrecht, The Netherlands. 

Heitkamp MA, W Franklin, CE Cerniglia (1988b) Microbial metabolism of polycyclic aromatic hydrocarbons isolation and characterization of a pyrene-degrading bacterium. Appl Environ Microbiol 54 2549-2555. 

Juhasz AL, R Naidu (2000) Bioremediation of high molecular weight polycyclic aromatic hydrocarbons a review of the microbial degradation of benzo[a]pyrene. Int Biodet Biodeg 45 57-88. 

DeWeerd KA, DL Bedard (1999) Use of balogenated benzoates and other halogenated aromatic compounds to stimnlate the microbial dechlorination of PCBs. Environ Sci Technol 33 2057-2063. 

Kulla HG, F Klausener, U Meyer, B Liideke, T Leisinger (1983) Interference of aromatic sulfo groups in the microbial degradation of the aza dyes Orange I and Orange II. Arch Microbiol 135 1-7. 

Meckenstock RU, B Morasch, R Warthmann, B Schink, E Annweiler, W Michaelis, HH Richnow (1999) C/ C isotope fractionation of aromatic hydrocarbons during microbial degradation. Environ Microbiol 1 409-425. 

Reviews on the microbial metabolism of hydrocarbons with biochemical aspects are available, and inclnde those of Britton (1984) on alkanes, and of Morgan and Watkinson (1994) that also includes cycloalkanes and some aromatic compounds. Virtually all the issues that are discussed in these recur in the examples that are used as illustration. Some broad generalizations are summarized ... 

Sutherland JB, E Rafii, AA Kahn, CE Cerniglia (1995) Mechanisms of polycyclic aromatic hydrocarbon degradation. In Microbial transformation and degradation of toxic organic chemicals (Eds LY Young and CE Cerniglia), pp. 269-306. Wiley-Liss, New York. 

Smith RV, Rosazza JP (1974) Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch Biochem Biophys 161(2) 551-558... 

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