scholarly journals Metabolism of biphenyl. 2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoate: the meta-cleavage product from 2,3-dihydroxybiphenyl by Pseudomonas putida

1973 ◽  
Vol 134 (4) ◽  
pp. 1063-1066 ◽  
Author(s):  
Danilo Catelani ◽  
Antonio Colombi ◽  
Claudia Sorlini ◽  
Vittorio Treccani
Keyword(s):  
Mass Spectrometry ◽  
Benzoic Acid ◽  
Pseudomonas Putida ◽  
Dienoic Acid ◽  
Cleavage Product ◽  
Degradative Pathway

1. 2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid was isolated and identified from washed suspensions of Pseudomonas putida incubated in the presence of 2,3-dihydroxybiphenyl. 2. Benzoic acid was isolated from reaction mixtures of crude cell-free extracts incubated with 2,3-dihydroxybiphenyl. 3. The presence in the same reaction mixtures of either 4-hydroxy-2-oxovalerate or 2-hydroxypenta-2,4-dienoate was suggested by mass spectrometry. 4. The degradative pathway of biphenyl is discussed.

scholarly journals Metabolism of biphenyl. Structure and physicochemical properties of 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid, the meta-cleavage product from 2,3-dihydroxybiphenyl by Pseudomonas putida

1974 ◽  
Vol 143 (2) ◽  
pp. 431-434 ◽  
Author(s):  
Danilo Catelani ◽  
Antonio Colombi
Keyword(s):  
Physicochemical Properties ◽  
Pseudomonas Putida ◽  
Dienoic Acid ◽  
Cleavage Product

The structure of 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid for the meta-cleavage product of 2,3-dihydroxybiphenyl by a Pseudomonas putida strain was demonstrated on the basis of its chemical and physicochemical properties and those of its derivatives.

The metabolism of cyclohexanecarboxylic acid and 3-cyclohexenecarboxylic acid by Pseudomonas putida

1982 ◽  
Vol 28 (12) ◽  
pp. 1324-1329 ◽  
Author(s):  
E. R. Blakley ◽  
B. Papish
Keyword(s):  
Benzoic Acid ◽  
Pseudomonas Putida ◽  
Sole Source ◽  
Oxidation Pathway ◽  
Cyclohexanecarboxylic Acid

A strain of Pseudomonas putida grew rapidly on cyclohexanecarboxylic acid as a sole source of carbon. A CoA-mediated β-oxidation pathway was induced for the metabolism of the compound. The organism could not utilize 3-cyclohexenecarboxylic acid as a sole source of carbon for growth, but cells grown on gluconate in the presence of 3-cyclohexenecarboxylic acid were induced to metabolize cyclohexanecarboxylic acid, benzoic acid, and catechol. Evidence is presented that 3-cyclohexenecarboxylic acid was slowly metabolized by a β-oxidation pathway and by a pathway involving benzoic acid as an intermediate. For this strain of Pseudomonas putida, 3-cyclohexenecarboxylic acid acts as an oxidizable, nongrowth substrate and induces the metabolism of cyclohexanecarboxylic acid and benzoic acid.

scholarly journals Chromenes and Prenylated Benzoic Acid Derivatives from the Liverwort Pedinophyllum interruptum

2004 ◽  
Vol 59 (7) ◽  
pp. 825-828 ◽  
Author(s):  
Hildegard Feld ◽  
David S. Rycroft ◽  
Josef Zapp
Keyword(s):  
Mass Spectrometry ◽  
Chemical Composition ◽  
Benzoic Acid ◽  
Diethyl Ether ◽  
Spectroscopic Techniques ◽  
Ether Extract ◽  
Benzoic Acid Derivatives ◽  
Diethyl Ether Extract

The chemical composition of a diethyl ether extract of the Scottish liverwort Pedinophyllum interruptum has been examined. Two new prenylated benzoic acid derivatives, methyl 2,6- dihydroxy-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate and methyl 2,4,6-trihydroxy-3-(3’-methyl- 2’-butenyl)benzoate, two new chromenes, methyl 5,7-dihydroxy-2,2-dimethyl-2H-chromene-6- carboxylate and methyl 7-hydroxy-5-methoxy-2,2-dimethyl-2H-chromene-8-carboxylate, and the two known chromenes methyl 8-hydroxy-2,2-dimethyl-2H-chromene-6-carboxylate and methyl 8- methoxy-2,2-dimethyl-2H-chromene-6-carboxylate were isolated. Methyl 2,4,6-trihydroxy-3-(3’- methyl-2’-butenyl)benzoate was unstable in air and was quickly converted into methyl 2,4,6- trihydroxy-3-(2’-hydroperoxy-3’-methyl-3’-butenyl)benzoate. All structures were elucidated by means of NMR spectroscopic techniques and mass spectrometry.

scholarly journals α-Pinene metabolism by Pseudomonas putida

1977 ◽  
Vol 168 (2) ◽  
pp. 315-318 ◽  
Author(s):  
N J Tudroszen ◽  
D P Kelly ◽  
N F Millis
Keyword(s):  
Pseudomonas Putida ◽  
Dienoic Acid ◽  
Enoic Acid ◽  
Alpha Pinene

By using metabolically altered mutants and acrylate, novel putative intermediates of alpha-pinene metabolism by Pseudomonas putida PIN11 were detected. They were characterized as 3-isopropylbut-3-enoic acid and (zeta)-2-methyl-5-isopropylhexa-2,5-dienoic acid.

Mechanismen der elektronenstoßinduzierten Methanoleliminierung aus ortho- und para-substituierten Benzoesäuremethylestern / Mechanisms of Electron Impact Induced Elimination of Methanol from ortho- and para-Substituted Benzoic Acid Methyl Ester

1976 ◽  
Vol 31 (6) ◽  
pp. 870-875 ◽  
Author(s):  
Rupert Herrmann ◽  
Helmut Schwarz
Keyword(s):  
Mass Spectrometry ◽  
Methyl Ester ◽  
Benzoic Acid ◽  
Electron Impact ◽  
Acid Methyl Ester ◽  
Ring Expansion ◽  
Acid Methyl ◽  
Π Complex ◽  
Fragmentation Reactions ◽  
Ring Expansion Reaction

Using deuterium labelled compounds the mechanisms of methyl as well as methanol elimination from the title compounds have been established. It can be shown that in the case of 4-methoxy-methyl benzoic acid methyl ester the unusual methanol elimination from the [M-methyl]+ ion probably proceeds via the formation of a π-complex and a ring expansion reaction. In addition to this novel fragmentation some ortho-effects and other fragmentation reactions useful for an analytical identification of the ortho/para-isomers by means of mass spectrometry are discussed.

Sign in / Sign up

Export Citation Format

Share Document