ChemInform Abstract: Short Chemical Synthesis of (-)-Chorismic Acid from (-)-Shikimic Acid.

ChemInform ◽  
2010 ◽  
Vol 22 (9) ◽  
pp. no-no
Author(s):  
H. B. WOOD ◽  
B. GANEM
1990 ◽  
Vol 112 (24) ◽  
pp. 8907-8909 ◽  
Author(s):  
Harold Blair Wood ◽  
Bruce Ganem

ChemInform ◽  
2010 ◽  
Vol 24 (25) ◽  
pp. no-no
Author(s):  
M. M. CAMPBELL ◽  
M. SAINSBURY ◽  
P. A. SEARLE

1969 ◽  
Vol 15 (1) ◽  
pp. 1-7 ◽  
Author(s):  
T. Leboeuf-Trudeau ◽  
J. de Repentigny ◽  
R. M. Frenette ◽  
S. Sonea

Tryptophan analogs known to act selectively on protein synthesis were used to study the effects of tryptophan depletion on the formation of Staphylococcus aureus (Wood 46 strain) toxic material. The production of toxin during growth and its presence in culture supernatants were followed by determining alpha hemolytic activity in rabbit blood agar, lethality for mice, and immunodiffusion patterns with staphylococcal antitoxins. The following results were obtained when the bacteria were grown in the presence of 4- and 5-methyltryptophans and 7-azatryptophan: (1) growth inhibition from 20 to 50%; (2) loss of alpha hemolytic activity; (3) inability of culture supernatants to kill mice; (4) decrease in the number of antigens precipitating with staphylococcal antitoxin and absence of reaction with purified alpha antitoxin. No significant effects were observed with 5-fluorotryptophan; 6-methyltryptophan was totally inactive. All inhibitions were reversed by L-tryptophan, anthranilic acid, and indole, but only partially by chorismic acid, and not at all by shikimic acid. These observations are suggestive of a predominant role of L-tryptophan in the synthesis of staphylococcal alpha toxin.


1998 ◽  
Vol 180 (9) ◽  
pp. 2541-2548 ◽  
Author(s):  
Dmitri V. Mavrodi ◽  
Vladimir N. Ksenzenko ◽  
Robert F. Bonsall ◽  
R. James Cook ◽  
Alexander M. Boronin ◽  
...  

ABSTRACT Pseudomonas fluorescens 2-79 produces the broad-spectrum antibiotic phenazine-1-carboxylic acid (PCA), which is active against a variety of fungal root pathogens. In this study, seven genes designated phzABCDEFG that are sufficient for synthesis of PCA were localized within a 6.8-kbBglII-XbaI fragment from the phenazine biosynthesis locus of strain 2-79. Polypeptides corresponding to allphz genes were identified by analysis of recombinant plasmids in a T7 promoter/polymerase expression system. Products of thephzC, phzD, and phzE genes have similarities to enzymes of shikimic acid and chorismic acid metabolism and, together with PhzF, are absolutely necessary for PCA production. PhzG is similar to pyridoxamine-5′-phosphate oxidases and probably is a source of cofactor for the PCA-synthesizing enzyme(s). Products of thephzA and phzB genes are highly homologous to each other and may be involved in stabilization of a putative PCA-synthesizing multienzyme complex. Two new genes, phzXand phzY, that are homologous to phzA andphzB, respectively, were cloned and sequenced from P. aureofaciens 30-84, which produces PCA, 2-hydroxyphenazine-1-carboxylic acid, and 2-hydroxyphenazine. Based on functional analysis of the phz genes from strains 2-79 and 30-84, we postulate that different species of fluorescent pseudomonads have similar genetic systems that confer the ability to synthesize PCA.


1968 ◽  
Vol 23 (2) ◽  
pp. 259-268 ◽  
Author(s):  
E. Leistner ◽  
M. H. Zenk

The biosynthesis of 5-hydroxy-1,4-naphthoquinone (juglone) was studied by supplying radioactive precursors to leaves of Juglans regia plants. A chemical degradation of the juglone molecule was devised (Fig. 1). With these methods it was shown that the ring atoms of shikimic acid are incorporated into the benzene ring of the quinone, while the carboxyl group of this acid is transformed to 50% into each of the keto groups of the quinone ring (C-atoms 1 and 4 of juglone. Tab. 3). This suggested a symmetrical molecule to be an intermediate in the formation of juglone — most probable 1,4-naphthoquinone. This compound was synthetized with 14C in the positions 2, 3, 9, and 10 and was found to be a good precursor of juglone in Juglans as well as for 2-hydroxy-1,4-naphthoquinone in Impatiens plants (Tab. 4) . 3,4-Dihydroxybenzaldehyde (Tab. 2) and chorismic acid (Tab. 7) which have been suggested previously as intermediates in the biosynthesis of naphthoquinones are no precursors of juglone. The source of three carbon atoms of the quinone nucleus remains to be determined; one or two of these carbon atoms (C2 and/or C3 of juglone) are formed from the methylen carbon of malonate (Tab. 5 and 6); surprisingly, however, the carboxyl carbons of malonic acid are not incorporated. The substitution of shikimic acid occures in the position 6 of this acid as could be judged from the degradation of juglone labelled with shikimic acid [ 1,2-14C] (Fig. 2; Tab. 3). 1,4-Naphthoquinone (or naphthohydroquinone) is postulated as an important intermediate in the biosynthesis of naphthoquinone derivatives in higher plants.


Synthesis ◽  
1993 ◽  
Vol 1993 (02) ◽  
pp. 179-193 ◽  
Author(s):  
M. M. Campbell ◽  
M. Sainsbury ◽  
P. A. Searle

1976 ◽  
Vol 22 (2) ◽  
pp. 237-244 ◽  
Author(s):  
A. Jones ◽  
L. C. Vining

Products obtained from the action of arylamine synthetase on [G-14C]chorismic acid were fractionated by gel filtration and ion exchange column chromatography to yield a partially purified radioactive component with an arylamine function. From its ultraviolet absorption spectrum and thin-layer chromatographic behaviour the product was considered to be p-aminophenylalanine and the identification was confirmed by co-crystallization with an authentic specimen. Specific deamination of the product with L-amino-acid oxidase indicated that it was the L- epimer. These results strengthen previous evidence that arylamine synthetase is at a branch point in the shikimic acid pathway, specifically diverting intermediates to the synthesis of chloramphenicol.


ChemInform ◽  
2010 ◽  
Vol 29 (30) ◽  
pp. no-no
Author(s):  
S. JIANG ◽  
G. SINGH

1965 ◽  
Vol 18 (8) ◽  
pp. 1227 ◽  
Author(s):  
JM Edwards ◽  
LM Jackman

The isolation and characterization of chorismic acid are described. The structure of the acid has been elucidated by spectroscopic methods and by chemical degradation as (IV). The relative and absolute stereochemistries have been established as identical with the corresponding centres in shikimic acid. Chorismic acid has been shown to differ from a compound for which Lingens and L�ck have claimed the structure (IV).


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