Catabolism of phenylacetic acid in Penicillium rubens. Proteome-wide analysis in response to the benzylpenicillin side chain precursor

2018 ◽  
Vol 187 ◽  
pp. 243-259 ◽  
Author(s):  
Mohammad-Saeid Jami ◽  
Juan-Francisco Martín ◽  
Carlos Barreiro ◽  
Rebeca Domínguez-Santos ◽  
María-Fernanda Vasco-Cárdenas ◽  
...  
Keyword(s):  
Phenylacetic Acid ◽  
Side Chain

THE IONIZATION CONSTANTS OF p-NITROPHENYLACETIC AND PHENYLMALONIC ACIDS

1933 ◽  
Vol 8 (5) ◽  
pp. 447-449 ◽  
Author(s):  
Steward Basterfield ◽  
James W. Tomecko
Keyword(s):  
Benzoic Acid ◽  
Nitro Group ◽  
Malonic Acid ◽  
Phenylacetic Acid ◽  
Ionization Constants ◽  
Side Chain ◽  
Cooh Group ◽  
Conductivity Data ◽  
Nitrobenzoic Acid ◽  
Phenylmalonic Acid

The ionization constants of p-nitrophenylacetic and phenylmalonic acids have been determined from conductivity data. The value of K for p-nitrophenylacetic acid at 25 °C. is 1.04 × 10−4, about twice that of phenylacetic acid. The nitro group in the nucleus has not as powerful an effect on the ionization when the COOH group is in the side chain as it has when both nitro group and COOH are in the nucleus. K for p-nitrobenzoic acid is six times as great as K for benzoic acid. K for phenylmalonic acid is 2. 77 × 10−3 as compared with 1.6 × 10−3 for malonic acid.

scholarly journals Biosynthesis of phytoquinones. Homogentisic acid: a precursor of plastoquinones, tocopherols and α-tocopherolquinone in higher plants, green algae and blue–green algae

1970 ◽  
Vol 117 (3) ◽  
pp. 593-600 ◽  
Author(s):  
G. R. Whistance ◽  
D. R. Threlfall
Keyword(s):  
Green Algae ◽  
Phenylacetic Acid ◽  
Higher Plants ◽  
Chlorella Pyrenoidosa ◽  
Homogentisic Acid ◽  
Side Chain ◽  
Methyl Groups ◽  
Blue Green Algae ◽  
Hydroxyphenylacetic Acid ◽  
Tracer Experiments

1. By means of 14C tracer experiments and isotope competition experiments the roles of d-tyrosine, p-hydroxyphenylpyruvic acid, p-hydroxyphenylacetic acid, phenylacetic acid, homogentisic acid and homoarbutin (2-methylquinol 4-β-d-glucoside) in the biosynthesis of plastoquinones, tocopherols and α-tocopherolquinone by maize shoots was investigated. It was established that d-tyrosine, p-hydroxyphenylpyruvic acid and homogentisic acid can all be utilized for this purpose, whereas p-hydroxyphenylacetic acid, phenylacetic acid and homoarbutin cannot. Studies on the mode of incorporation of d-tyrosine, p-hydroxyphenylpyruvic acid and homogentisic acid showed that their nuclear carbon atoms and the side-chain carbon atom adjacent to the nucleus give rise (as a C6-C1 unit) to the p-benzoquinone rings and nuclear methyl groups (one in each case) of plastoquinone-9 and α-tocopherolquinone and the aromatic nuclei and nuclear methyl groups (one in each case) of γ-tocopherol and α-tocopherol. 2. By using [14C]-homogentisic acid it has been shown that homogentisic acid is also a precursor of plastoquinone, tocopherols and α-tocopherolquinone in the higher plants Lactuca sativa and Rumex sanguineus, the green algae Chlorella pyrenoidosa and Euglena gracilis and the blue–green alga Anacystis nidulans.

Microbial degradation of [14C]polystyrene and 1,3-diphenylbutane

1978 ◽  
Vol 24 (7) ◽  
pp. 798-803 ◽  
Author(s):  
M. Sielicki ◽  
D. D. Focht ◽  
J. P. Martin
Keyword(s):  
Microbial Degradation ◽  
Soil Microorganisms ◽  
Phenylacetic Acid ◽  
Side Chain ◽  
Microbial Oxidation ◽  
Initial Examination ◽  
Enrichment Cultures ◽  
Oxidative Reactions ◽  
Degradation Rates ◽  
Carbon Fragment

Microbial degradation of [β-14C]polystyrene and 1,3-diphenylbutane, a compound structurally representing the smallest repeating unit of styrene (dimer), was investigated in soil and liquid enrichment cultures. Degradation rates in soil, as determined by 14CO2 evolution from applied [14C]polystyrene, varied from 1.5 to 3.0% for a 4-month period. Although relatively low, these percentages were 15 to 30 times greater than values previously reported. Enrichment cultures, containing 1,3-diphenylbutane as the only carbon source, were used to determine the mechanisms of microbial oxidation of the polymer chain ends. Metabolism of 1,3-diphenylbutane appeared to involve the attack by a monooxygenase to form 2-phenyl-4-hydroxyphenylbutane followed by a further oxidation and subsequent fission of the benzene ring to yield 4-phenylvaleric acid and an unidentified 5-carbon fragment via the classic meta-fission pathway. Phenylacetic acid was probably formed from 4-phenylvaleric acid by subsequent β-oxidation of the side chain, methyl-oxidation, and decarboxylation. An initial examination of the population of microorganisms in the diphenylbutane enrichment cultures indicated that these oxidative reactions are carried out by common soil microorganisms of the genera Bacillus, Pseudomonas, Micrococcus, and Nocardia.

THE METABOLISM OF AROMATIC COMPOUNDS WITH DIFFERENT SIDE CHAINS BY A PSEUDOMONAS

1967 ◽  
Vol 13 (7) ◽  
pp. 761-769 ◽  
Author(s):  
E. R. Blakley
Keyword(s):  
Aromatic Ring ◽  
Aromatic Compounds ◽  
Phenylacetic Acid ◽  
Oxidative Degradation ◽  
Homogentisic Acid ◽  
Side Chain ◽  
Hydroxybenzoic Acid ◽  
Side Chains ◽  
Acid Pathway ◽  
Phenylbutyric Acid

A strain of Pseudomonas previously used to study the oxidative degradation of phenylacetic acid and phenylpropionic acid has been used to study the degradation of p-hydroxybenzoic acid, L-tyrosine, L-phenylalanine, phenylbutyric acid, and phenylvaleric acid. p-Hydroxybenzoic acid was converted to 3, 4-dihydroxy-benzoic acid and the aromatic ring was cleaved between carbons 3 and 4. Previous results showed that cleavage of 3, 4-dihydroxyphenylacetic acid occurred between carbons 2 and 3. Phenylalanine and tyrosine were metabolized by the homogentisic acid pathway. These results, together with results of previous work, suggest that the pathway used for the degradation of aromatic compounds by this organism varies with the nature of the side chain. The metabolism of aromatic compounds with side chains longer than three carbons appears to involve oxidative shortening of the side chain prior to cleavage of the aromatic ring.

scholarly journals On the Enigma of Glutathione-Dependent Styrene Degradation inGordonia rubripertinctaCWB2

2018 ◽  
Vol 84 (9) ◽  
Author(s):  
Thomas Heine ◽  
Juliane Zimmerling ◽  
Anne Ballmann ◽  
Sebastian Bruno Kleeberg ◽  
Christian Rückert ◽  
...  
Keyword(s):  
Phenylacetic Acid ◽  
Styrene Oxide ◽  
Sole Source ◽  
Degradation Pathway ◽  
Side Chain ◽  
Benzene Derivatives ◽  
Biotechnological Applications ◽  
Content Type ◽  
Styrene Derivatives ◽  
Specific Degradation

ABSTRACTAmong bacteria, only a single styrene-specific degradation pathway has been reported so far. It comprises the activity of styrene monooxygenase, styrene oxide isomerase, and phenylacetaldehyde dehydrogenase, yielding phenylacetic acid as the central metabolite. The alternative route comprises ring-hydroxylating enzymes and yields vinyl catechol as central metabolite, which undergoesmeta-cleavage. This was reported to be unspecific and also allows the degradation of benzene derivatives. However, some bacteria had been described to degrade styrene but do not employ one of those routes or only parts of them. Here, we describe a novel “hybrid” degradation pathway for styrene located on a plasmid of foreign origin. As putatively also unspecific, it allows metabolizing chemically analogous compounds (e.g., halogenated and/or alkylated styrene derivatives).Gordonia rubripertinctaCWB2 was isolated with styrene as the sole source of carbon and energy. It employs an assembled route of the styrene side-chain degradation and isoprene degradation pathways that also funnels into phenylacetic acid as the central metabolite. Metabolites, enzyme activity, genome, transcriptome, and proteome data reinforce this observation and allow us to understand this biotechnologically relevant pathway, which can be used for the production of ibuprofen.IMPORTANCEThe degradation of xenobiotics by bacteria is not only important for bioremediation but also because the involved enzymes are potential catalysts in biotechnological applications. This study reveals a novel degradation pathway for the hazardous organic compound styrene inGordonia rubripertinctaCWB2. This study provides an impressive illustration of horizontal gene transfer, which enables novel metabolic capabilities. This study presents glutathione-dependent styrene metabolization in an (actino-)bacterium. Further, the genomic background of the ability of strain CWB2 to produce ibuprofen is demonstrated.

scholarly journals Genetic Modification of mfsT Gene Stimulating the Putative Penicillin Production in Monascus ruber M7 and Exhibiting the Sensitivity towards Precursor Amino Acids of Penicillin Pathway

2019 ◽  
Vol 7 (10) ◽  
pp. 390
Author(s):  
Ramzan ◽  
Safiullah Virk ◽  
Muhammad ◽  
Ahmed ◽  
Yuan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Gene Deletion ◽  
Phenylacetic Acid ◽  
Intermediate Compound ◽  
Penicillin G ◽  
Side Chain ◽  
Penicillin Production ◽  
Monascus Ruber ◽  
Traffic System ◽  
Transporter Protein

: The biosynthesis of penicillin G (PG) is compartmentalized, which forces penicillin and its intermediates to cross the membrane barriers. Although many aspects around the penicillin intermediates traffic system remain unclosed, the transmembrane transporter protein involvement has been only predicted. In the present work, detection of PG and isopenicillin N (IPN) in Monascus ruber M7 was performed and functions of mfst gene as a transporter were investigated by the combination of gene deletion (Δmfst) complementation (ΔmfsT::mfsT) and overexpression (M7::PtrpC-mfsT). While, the feeding of PG pathway precursor side chain and amino acids, i.e., phenylacetic acid, D-valine, and L-cysteine was performed for the interpretation of mfsT gene role as an intermediate transporter. The results showed that, the feeding of phenylacetic acid, D-valine, and L-cysteine possessed a significant effect on morphologies, secondary metabolites (SMs) production of all above-mentioned strains including M. ruber M7. The results of UPLC-MS/MS revealed that, ΔmfsT interrupt the penicillin G (PG) production in M. ruber M7 by blocking the IPN transportation, while PG and IPN produced by the ΔmfsT::mfsT have been recovered the similar levels to those of M. ruber M7. Conclusively, these findings suggest that the M. ruber M7 is, not only a PG producer, but also, indicate that the mfsT gene is supposed to play a key role in IPN intermediate compound transportation during the PG production in M. ruber M7.

Electroluminescent properties of side-chain naphthalimide-derivated polymers

1998 ◽  
Vol 95 (6) ◽  
pp. 1351-1354 ◽  
Author(s):  
C.-M. Bouché ◽  
P. Le Barny ◽  
H. Facoetti ◽  
F. Soyer ◽  
P. Robin
Keyword(s):  
Side Chain

Evidence for Impaired Hepatic Vitamin K1 Metabolism in Patients Treated with N-Methyl-Thiotetrazole Cephalosporins

1984 ◽  
Vol 51 (03) ◽  
pp. 358-361 ◽  
Author(s):  
H Bechtold ◽  
K Andrassy ◽  
E Jähnchen ◽  
J Koderisch ◽  
H Koderisch ◽  
...  
Keyword(s):  
Protein C ◽  
Oral Intake ◽  
Bleeding Complications ◽  
Side Chain ◽  
Acute Administration ◽  
Vitamin K1 ◽  
New Class ◽  
Parenteral Alimentation ◽  
Hepatocellular Regeneration ◽  
Echis Carinatus

SummaryIn 8 patients on no oral intake and with parenteral alimentation, administration of cephalosporins with N-methyl-thiotetrazole side chain (moxalactam, cefamandole), was associated with prolongation of prothrombin time, appearance in the circulation of descarboxy-prothrombin (counter immunoelectrophoresis and echis carinatus assay) and diminution of protein C. Acute administration of 10 mg vitamin Ki was followed by the transient appearance of vitamin K1 2,3-epoxide, indicating an impaired hepatocellular regeneration of vitamin K1 from the epoxide. Impaired hepatic vitamin K1 metabolism, tentatively ascribed to the N-methyl-thiotetrazole group, is one (but possibly not the only) cause of bleeding complications and depression of vitamin K1dependent procoagulants in patients treated with the new class of cephalosporins.

METABOLISM OF 17α-HYDROXYPROGESTERONE-4-14C-17α-CAPROATE BY HOMOGENATES OF RAT LIVER AND HUMAN PLACENTA

1961 ◽  
Vol 36 (4) ◽  
pp. 511-519 ◽  
Author(s):  
Margaret Wiener ◽  
Charles I. Lupa ◽  
E. Jürgen Plotz
Keyword(s):  
Rat Liver ◽  
Human Placenta ◽  
Steric Hindrance ◽  
Placental Tissue ◽  
Caproic Acid ◽  
Major Product ◽  
Side Chain ◽  
Anaerobic Conditions ◽  
Prolonged Action ◽  
Long Acting

ABSTRACT 17α-hydroxyprogesterone-4-14C-17α-caproate (HPC), a long-acting progestational agent, was incubated with homogenates of rat liver and human placenta. The rat liver was found to reduce Ring A of HPC under anaerobic conditions to form allopregnane-3β,17α-diol-20-one-17α-caproate and pregnane-3β,17α-diol-20-one-17α-caproate, the allopregnane isomer being the major product. The caproic acid ester was neither removed nor altered during the incubation. Placental tissue did not attack HPC under conditions where the 20-ketone of progesterone was reduced. It is postulated that this absence of attack on the side chain is due to steric hindrance from the caproate ester, and that this may account for the prolonged action of HPC.

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