Biosynthesis of isochorismate in Klebsiella pneumoniae: origin of O-2

1991 ◽  
Vol 37 (4) ◽  
pp. 276-280 ◽  
Author(s):  
Lolita O. Zamir ◽  
Kenneth A. Devor ◽  
Roy A. Jensen ◽  
Robert Tiberio ◽  
Françoise Sauriol ◽  
...  
Keyword(s):  
Amino Acids ◽  
Natural Products ◽  
Mass Spectra ◽  
Biosynthetic Pathway ◽  
Fast Atom Bombardment ◽  
Claisen Rearrangement ◽  
Aromatic Amino Acids ◽  
Hydroxyl Group ◽  
Chorismic Acid ◽  
Important Branch

The shikimate metabolites are key precursors to a large number of natural products, including aromatic amino acids. Chorismic acid is an important branch point in the biosynthetic pathway to aromatic amino acids. Chorismic acid is also unique among natural products since it is the only compound known to undergo an enzymatic Claisen rearrangement. A metabolite of chorismic acid, isochorismic acid, first observed in Aerobacter aerogenes differs in its chemical structure by the location of the hydroxyl group and the double bonds. Isochorismic acid is a precursor to a growing number of shikimate-derived metabolites. Isochorismic acid has also been postulated to be an intermediate of m-carboxyaromatic amino acids, implying another enzymatic Claisen rearrangement. In this publication, we have isolated isochorismate synthase and found that on lyophilization the enzyme is stable for at least 6 months at −20 °C. Incubation of chorismate with this preparation in water enriched with 18O led to incorporation of one atom of 18O as proven from the fast atom bombardment mass spectra of the HPLC purified derived isochorismate. Key words: chorismate, isochorismate, rearrangement, H218O, isochorismate synthetase.

Laser mass spectra of simple aliphatic and aromatic amino acids

1985 ◽  
Vol 57 (3) ◽  
pp. 698-704 ◽  
Author(s):  
Cass D. Parker ◽  
David M. Hercules
Keyword(s):  
Amino Acids ◽  
Mass Spectra ◽  
Aromatic Amino Acids

STUDIES ON THE BIOSYNTHESIS OF VOLUCRISPORIN: II. METABOLISM OF SOME PHENYLPROPANOID COMPOUNDS BY VOLUCRISPORA AURANTIACA HASKINS

1966 ◽  
Vol 44 (4) ◽  
pp. 403-413 ◽  
Author(s):  
P. Chandra ◽  
G. Read ◽  
L. C. Vining
Keyword(s):  
Amino Acids ◽  
Cinnamic Acid ◽  
Biosynthetic Pathway ◽  
Shikimic Acid ◽  
Aromatic Amino Acids ◽  
Hydroxycinnamic Acid ◽  
Phenyllactic Acid ◽  
Radioactive Substrate

DL-Phenyllactic acid-α-14C, DL-phenylserine-α-14C, L-phenylalanine-carboxyl-14C, and shikimic acid-U-14C were incorporated into phenylalanine and tyrosine isolated from mycelial hydrolysates of Volucrispora aurantiaca as well as into volucrisporin. DL-m-Tyrosine-carboxyl-14C was incorporated into volucrisporin but not into the aromatic amino acids. L-Tyrosine-β-14C, cinnamic acid-α-14C, and m-hydroxycinnamic acid-α-14C were metabolized by the fungus but did not serve as precursors of volucrisporin or of mycelial phenylalanine. The results are consistent with the concept of a biosynthetic pathway to volucrisporin via phenylpyruvic and m-hydroxyphenylpyruvic acids. Substantial amounts of each radioactive substrate fed to V. aurantiaca PRL 1952 were incorporated into a brown melanoid pigment.

scholarly journals Physiological performance of glyphosate and imazamox mixtures on Amaranthus palmeri sensitive and resistant to glyphosate

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Manuel Fernández-Escalada ◽  
Ainhoa Zulet-González ◽  
Miriam Gil-Monreal ◽  
Mercedes Royuela ◽  
Ana Zabalza
Keyword(s):  
Amino Acids ◽  
Biosynthetic Pathway ◽  
Aromatic Amino Acids ◽  
Transcriptional Level ◽  
Amaranthus Palmeri ◽  
Physiological Effects ◽  
Herbicide Application ◽  
Transcriptional Pattern ◽  
Herbicide Mixtures ◽  
Branched Chain

AbstractThe herbicides glyphosate and imazamox inhibit the biosynthetic pathway of aromatic amino acids (AAA) and branched-chain amino acids (BCAA), respectively. Both herbicides share several physiological effects in the processes triggered in plants after herbicide application that kills the plant, and mixtures of both herbicides are being used. The aim of this study was to evaluate the physiological effects in the mixture of glyphosate and imazamox in glyphosate-sensitive (GS) and -resistant (GR) populations of the troublesome weed Amaranthus palmeri. The changes detected in the physiological parameters after herbicide mixtures application were similar and even less to the changes detected after individual treatments. This pattern was detected in shikimate, amino acid and carbohydrate content, and it was independent of the EPSPS copy number, as it was detected in both populations. In the case of the transcriptional pattern of the AAA pathway after glyphosate, interesting and contrary interactions with imazamox treatment were detected for both populations; enhancement of the effect in the GS population and alleviation in the GR population. At the transcriptional level, no cross regulation between AAA and BCAA inhibitors was confirmed. This study suggests that mixtures are equally or less toxic than herbicides alone, and would implicate careful considerations when applying the herbicide mixtures.

Bioorganic Synthesis

2016 ◽  
Author(s):  
Gary W. Morrow
Keyword(s):  
Organic Chemistry ◽  
Amino Acids ◽  
Natural Products ◽  
Organic Compounds ◽  
Undergraduate Students ◽  
Unsaturated Fatty Acids ◽  
Shikimate Pathway ◽  
Aromatic Amino Acids ◽  
Nitrogenous Compounds ◽  
Bioorganic Synthesis

Building on the foundation of a one-year introductory course in organic chemistry, Bioorganic Synthesis: An Introduction focuses on organic reactions involved in the biosynthesis of naturally-occurring organic compounds with special emphasis on natural products of pharmacological interest. The book is designed specifically for undergraduate students, rather than as an exhaustive reference work for graduate students or professional researchers and is intended to support undergraduate courses for students majoring in chemistry, biochemistry, biology, pre-medicine, and bioengineering programs who would benefit from a deeper understanding of the chemical logic of reactions carried out in organisms and the origins and uses of the important organic compounds they often produce. The book assumes no prior background in biochemistry and consists of eight chapters: i) a brief review of relevant topics from introductory organic chemistry; ii) presentation of essential organic and biochemical reactions used throughout the book along with a brief introduction to coenzymes; iii) review of basic carbohydrates and the biosynthesis of amino acids; iv) the terpenoid pathway for biosynthesis of all important classes of terpenoids and steroids; v) the acetate pathway for biosynthesis of saturated and unsaturated fatty acids, prostaglandins and acetate-derived polyketide natural products; vi) the biosynthesis of the shikimate pathway products derived from aromatic amino acids; vii) an introduction to biosynthesis of major alkaloids and related nitrogenous compounds; and viii) an overview of laboratory organic synthesis as it relates to the challenges faced by synthetic and medicinal chemists who must recreate intricate natural product structures in the laboratory.

scholarly journals The Biotransformation of Aromatic Amino Acids by Phoma macrostoma

2010 ◽  
Vol 5 (1) ◽  
pp. 1934578X1000500
Author(s):  
Yevgeniya Tyagunova ◽  
John L. Sorensen
Keyword(s):  
Amino Acids ◽  
Natural Products ◽  
Amino Acid ◽  
Aromatic Amino Acids ◽  
Major Metabolite

A search for natural products produced in fermentation cultures of a strain of Phoma macrostoma led to the identification of tyrosol as the major metabolite produced by this organism. The addition of the amino acid tyrosine to growing fermentation cultures of P. macrostoma resulted in an increase in the production of tyrosol. It was subsequently determined that this strain of P. macrostoma was also capable of the biotransformation of other amino acids into similar alcohols.

scholarly journals Biosynthesis of ribose-5-phosphate and erythrose-4-phosphate in archaea: a phylogenetic analysis of archaeal genomes

Archaea ◽  
2005 ◽  
Vol 1 (5) ◽  
pp. 347-352 ◽  
Author(s):  
Tim Soderberg
Keyword(s):  
Amino Acids ◽  
Phylogenetic Analysis ◽  
Biosynthetic Pathway ◽  
Aromatic Amino Acids ◽  
Amino Acid Biosynthesis ◽  
Pentose Phosphate ◽  
Acid Biosynthesis ◽  
Potential Explanation ◽  
Archaeal Species ◽  
Genes Encoding

A phylogenetic analysis of the genes encoding enzymes in the pentose phosphate pathway (PPP), the ribulose monophosphate (RuMP) pathway, and the chorismate pathway of aromatic amino acid biosynthesis, employing data from 13 complete archaeal genomes, provides a potential explanation for the enigmatic phylogenetic patterns of the PPP genes in archaea. Genomic and biochemical evidence suggests that three archaeal species (Methanocaldococcus jannaschii,Thermoplasma acidophilumandThermoplasma volcanium) produce ribose-5-phosphate via the nonoxidative PPP (NOPPP), whereas nine species apparently lack an NOPPP but may employ a reverse RuMP pathway for pentose synthesis. One species (Halobacteriumsp. NRC-1) lacks both the NOPPP and the RuMP pathway but may possess a modified oxidative PPP (OPPP), the details of which are not yet known. The presence of transketolase in several archaeal species that are missing the other two NOPPP genes can be explained by the existence of differing requirements for erythrose-4-phosphate (E4P) among archaea: six species use transketolase to make E4P as a precursor to aromatic amino acids, six species apparently have an alternate biosynthetic pathway and may not require the ability to make E4P, and one species (Pyrococcus horikoshii) probably does not synthesize aromatic amino acids at all.

scholarly journals Biosynthesis of dihydroquercetin in Escherichia coli from glycerol

2020 ◽  
Author(s):  
Seon Young Park ◽  
Dongsoo Yang ◽  
Shin Hee Ha ◽  
Sang Yup Lee
Keyword(s):  
Escherichia Coli ◽  
Natural Products ◽  
Biosynthetic Pathway ◽  
Carbon Sources ◽  
Aromatic Amino Acids ◽  
Engineering Model ◽  
Producer Strain ◽  
E Coli ◽  
One Step ◽  
First Time

AbstractPhenylpropanoids are a group of diverse natural products derived from aromatic amino acids. Although their demands are high both as drugs and nutraceuticals, their production mainly depends on inefficient extraction from plants. To achieve sustainable production of phenylpropanoids, engineering model microorganisms such as Escherichia coli has been sought, but most strains require supplementation of expensive precursors. Here, we report one-step production of a representative phenylpropanoid, dihydroquercetin (DHQ), from simple carbon sources in E. coli for the first time. The best DHQ producer strain capable of producing 239.4 mg/L of DHQ from glycerol was obtained by optimizing the biosynthetic pathway and engineering the signal peptide of cytochrome P450 (TT7) from Arabidopsis thaliana. The engineered plant P450 could produce a significantly higher titer of DHQ than a bacterial monooxygenase, showing the potential of employing plant P450s for the production of diverse natural products that has been previously difficult in bacterial hosts. This study will serve as a guideline for industrial production of pharmaceutically important yet complex natural products.

Sign in / Sign up

Export Citation Format

Share Document