Evidence for β-Oxidation in the Metabolism of Saturated Aliphatic Hydrocarbons by Soil Species of Nocardia

Webley, D. M.; Duff, R. B.; Farmer, V. C.

doi:10.1038/1781467b0

Cited by 56 publications

(33 citation statements)

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“…The alkyl chains in phenylalkanes or alkylcyclohexanes with lesser chain length (C 2 to C 4 ) were also oxidized cometabolically by a Nocardia species with n-alkanes only (12). In contrast to these results, phenylalkanes with greater chain lengths (C 9 to C 18 ) were transformed by nocardiae at the alkyl chain and served as inductor and as a source of carbon and energy without the necessity of an additional alkane induction (12,51).…”

Section: Transformation Of N-(2-hexylamino-4-phenylimidazol-1-yl)-acementioning

confidence: 66%

“…4), though further ␤-oxidation to the level of an acetic acid derivative was not detected. Webley et al (51) reported the rapid conversion of 2-phenylpropionic acid (oxidation product of phenyl alkanes) via cinnamic to benzoic acid by two strains of Nocardia and the failure of such a chain shortening with 2-␣-naphthylpropionic acid (oxidation product of 2-␣-naphthyl alkanes). The lack of ␤-oxidation was attributed by these authors (51) to an electronic or steric effect of the larger nucleus of 2-␣-naphthylpropionic acid.…”

Section: Transformation Of N-(2-hexylamino-4-phenylimidazol-1-yl)-acementioning

confidence: 99%

“…There exist several examples for the oxidation of alkyl residues in more hydrophilic compounds than n-alkanes, e.g., the oxidation of alkyl groups of phenyl alkanes (12,16,51), alkyl benzene sulfonates (55), 2,5-alkyl thiophenes (17), and 6-alkyl-2-pyrones (40). The transformation of decyl-and hexadecyltriammonium bromides was described by Dean-Raymond and Alexander (13) and the degradation of long-chain n-alkylcyclohexanes by Dutta and Harayama (16).…”

Section: Transformation Of N-(2-hexylamino-4-phenylimidazol-1-yl)-acementioning

confidence: 99%

“…Alkane-oxidizing bacteria should be able to oxidize the terminal methyl group of the alkylamino substituent of the N-(2-alkylamino-4-phenylimidazol-1-yl)-acetamides to yield the desired imidazol-2-yl amino acids, because the most common pathway of oxidation of alkyl chains is the monoterminal oxidation via an alcohol and an aldehyde intermediate (37,41) to the corresponding carboxylic acid. Such microbial transformation has also been found for alkyl substituents of aromatics and heteroaromatics such as phenyl alkanes (51), alkyl benzene sulfonates (55), 2,5-alkyl thiophenes (17), or 6-alkyl-2-pyrones (40) and offers an attractive route for organic synthesis to produce novel aromatic and heteroaromatic substituted aliphatic acids.…”

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Synthesis of Imidazol-2-yl Amino Acids by Using Cells from Alkane-Oxidizing Bacteria

Mikolasch

Hammer

Schauer

2003

Appl Environ Microbiol

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Sixty-one strains of alkane-oxidizing bacteria were tested for their ability to oxidize N-(2-hexylamino-4-phenylimidazol-1-yl)-acetamide to imidazol-2-yl amino acids applicable for pharmaceutical purposes. After growth with n-alkane, 15 strains formed different imidazol-2-yl amino acids identified by chemical structure analysis (mass and nuclear magnetic resonance spectrometry). High yields of imidazol-2-yl amino acids were produced by the strains Gordonia rubropertincta SBUG 105, Gordonia terrae SBUG 253, Nocardia asteroides SBUG 175, Rhodococcus erythropolis SBUG 251, and Rhodococcus erythropolis SBUG 254. Biotransformation occurred via oxidation of the alkyl side chain and produced 1-acetylamino-4-phenylimidazol-2-yl-6-aminohexanoic acid and the butanoic acid derivative. In addition, the acetylamino group of these products and of the substrate was transformed to an amino group. The product pattern as well as the transformation pathway of N-(2-hexylamino-4-phenylimidazol-1-yl)-acetamide differed in the various strains used.Substitued imidazoles have been extensively used in medicine and agriculture. The recognition early in the last century that histamine, 2-(4-imidazolyl)ethylamine, acts as a messenger molecule in cell-to-cell communication (3,10,11) led to the development and use of antihistamine drugs, defined as H 1 , H 2 , and H 3 receptor antagonists with structures related to histamine (4, 46). Burimamid and cimetidin were described as selective H 2 receptor antagonists (4, 5), and phenoxyalkyl imidazoles have been developed as potent H 3 receptor antagonists (19). Some substituted imidazoles have antifungal activities (14,15,39,44,49,53,54), while various 1-substituted imidazoles have anticonvulsant properties (9, 21, 22, 24-26, 38, 43, 44). Furthermore, the biologically active angiotensin II receptor antagonists have an imidazole moiety (1). Apart from Nbenzylimidazoles (8), eprosartan (36), and related compounds (6, 32), imidazolylalkylamino acids are also potent angiotensin II receptor antagonists (28).Because of the manifold biological activities of imidazole derivatives, we investigated whether novel imidazol-2-yl amino acids, applicable for pharmaceutical purposes, might be synthesized from N-(2-alkylamino-4-phenylimidazol-1-yl)-acetamides by using microbial biotransformation reactions. Alkane-oxidizing bacteria should be able to oxidize the terminal methyl group of the alkylamino substituent of the N-(2-alkylamino-4-phenylimidazol-1-yl)-acetamides to yield the desired imidazol-2-yl amino acids, because the most common pathway of oxidation of alkyl chains is the monoterminal oxidation via an alcohol and an aldehyde intermediate (37,41) to the corresponding carboxylic acid. Such microbial transformation has also been found for alkyl substituents of aromatics and heteroaromatics such as phenyl alkanes (51), alkyl benzene sulfonates (55), 2,5-alkyl thiophenes (17), or 6-alkyl-2-pyrones (40) and offers an attractive route for organic synthesis to produce novel aromatic and heteroaromatic substituted...

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Section: Transformation Of N-(2-hexylamino-4-phenylimidazol-1-yl)-acementioning

confidence: 66%

Section: Transformation Of N-(2-hexylamino-4-phenylimidazol-1-yl)-acementioning

confidence: 99%

Section: Transformation Of N-(2-hexylamino-4-phenylimidazol-1-yl)-acementioning

confidence: 99%

mentioning

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Synthesis of Imidazol-2-yl Amino Acids by Using Cells from Alkane-Oxidizing Bacteria

Mikolasch

Hammer

Schauer

2003

Appl Environ Microbiol

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“…Hydrocarbon oxidation t o acids of shorter chain length has also beell observed (10) and appareiltly proceeds by P-oxidation. With Tor~ilopsis magnoliae the probable course of reaction is oxidation t o the fatty acid, and for longer-chain substailces reduction t o 18 carbon atoms and then hydroxylation as before.…”

Section: E~zzyrnic Reactio~zs Involvedmentioning

confidence: 99%

The Fermentation of Long-Chain Compounds by Torulopsis Magnoliae: I. Structures of the Hydroxy Fatty Acids Obtained by the Fermentation of Fatty Acids and Hydrocarbons

Tulloch¹,

Spencer²,

Gorin³

1962

Can. J. Chem.

144

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The yield of estracell~~lar glycolipid producetl by Torlrlopsis ttzugi~olicre is increased threeto five-fold by the addition of s~~i t a b l e compo~~ncls to the growing culture. 'The supplement, which can be a long-chain acid, ester, hydrocarbon, or glyceride, is hydrorylated and converted to hytlrory fatty acid sopl~orosicles. Fatty esters of all chain I c~~g t h s from Clo to CE, incl~icling several ~~n s a t~~r a t e d esters, and even-numbered hydrocarbons from CIG to Clr are readily fermented. Shorter-chain compounds are ~~s e d poorly or not a t all. \\'ith compounds of 16 to 18 carbon atoms, hydroxylation occurs a t the terminal or penultimate carbon atom, depending on degree of ~~nsaturation and chain length. Substrates of more than 18 carbon atoms are mainly recl~~ced in chai11 le~igth by one or more two-carbon nits and hydrosylatecl, giving C1, or C1s acids with the hydrosyl group 011 the pen~~ltimate carbon atom. 'The various enzymic reactions which occur tluring the fermentation are discussed.T h e estracellular oil produced by a particular strain of To.r,idopsis magnoliae in submerged culture has beell the subject of a n earlier investigation (1). I t is heavier than water and consists of a mixture of liydroxy fatty acid glycosides of partially acetylated sophorose. The major components of the fatty acid portion of this "normal procluct" were 17-L-l~ydroxyoctadecanoic acid and 17-L-hydrosy-9-octadecci~oic acid. Several minor coinponeilts have since bee11 identified as described below.I t has now been founcl that many long-chain compounds can be fermented bj-7'orulofis%.s nzagnobiae with a substantial increase in the yield of glycolipid. T h e proclucts are partially acetylatecl glycosides of hydroxy fatty acids as before, b u t the composition of the fatty acid portion varies with the substance aclcled. T o study this variation the glycolipids were subjected to acid metlianolysis ancl the hydroxy fatty acicl esters producecl were analyzed by gas-licluid chromatography (GLC).The compositions iound when various fatty acid esters are incorporatecl into the medium are compared in Table I with that oi the "normal product". Two hyclroxy palmitic acicls are the major components of the hyclroxy acicls obtained irom thc fermentation oi methyl palmitate and also occur as minor components of the "normal procluct". One was shown to be 16-hydroxypalmitic ncicl by oxidation to liexadecanedioic acid. T h e other was thought to be 15-1~yclroxypalmitic acicl by analogy with the 17-h~-drosy acicl previously founcl (1). Bromiiiation-clehydrobromination followed by oxidation with permanganate-periodate gave tetradecanedioic acid ( 2 ) , and the clerived 0x0 acicl was shown to be iclentical with synthetic 15-oxopalmitic acid. T h e starting material for preparation of the latter was erucic acid; cis hydroxylation gave th.reo-13,14-dil1yc1rox~~-behenic acid, which, after lead tetraacetate oxidation ancl hydrogenation, gave 13-hydroxytridecanoic acid. The w-Ilydroxy acid \\?as brominated to yield 13-bromotridecan...

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The Mechanisms of Microbial Oxidations of Petroleum Hydrocarbons

Linden¹,

Thijsse²

1965

Advances in Enzymology - And Related Areas of Molecular Biology

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Evidence for β-Oxidation in the Metabolism of Saturated Aliphatic Hydrocarbons by Soil Species of Nocardia

Cited by 56 publications

References 3 publications

Synthesis of Imidazol-2-yl Amino Acids by Using Cells from Alkane-Oxidizing Bacteria

Synthesis of Imidazol-2-yl Amino Acids by Using Cells from Alkane-Oxidizing Bacteria

The Fermentation of Long-Chain Compounds by Torulopsis Magnoliae: I. Structures of the Hydroxy Fatty Acids Obtained by the Fermentation of Fatty Acids and Hydrocarbons

The Mechanisms of Microbial Oxidations of Petroleum Hydrocarbons

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