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(6S)-6-fluoroshikimic Acid
(6''S'')-6-Fluoroshikimic acid is an antibacterial agent acting on the aromatic biosynthetic pathway. It may be used against ''Plasmodium falciparum'', the causative agent of malaria. The molecule is targeting the enzymes of the shikimate pathway. This metabolic pathway is not present in mammals. The mechanism of action of the molecule is not through the inhibition of chorismate synthase but by the inhibition of 4-aminobenzoic acid synthesis. The use of the molecule led to resistances in ''Escherichia coli''. See also * Shikimic acid Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower ''shi ... References Antibiotics Fluorinated carboxylic acids Cyclitols Halohydrins Cyclohexenes {{antibiotic-stub ...
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Antimicrobial Agents And Chemotherapy
''Antimicrobial Agents and Chemotherapy'' is a peer-reviewed scientific journal published by the American Society for Microbiology. It covers antimicrobial, antiviral, antifungal, and antiparasitic agents and chemotherapy. The editor-in-chief is Cesar A. Arias (University of Texas Health Science Center at Houston). It was established in 1972 by Gladys Lounsbury Hobby. __TOC__ Abstracting and indexing The journal is abstracted and indexed in: According to the ''Journal Citation Reports'', its 2021 impact factor The impact factor (IF) or journal impact factor (JIF) of an academic journal is a scientometric index calculated by Clarivate that reflects the yearly mean number of citations of articles published in the last two years in a given journal, as i ... is 5.938, ranking it 51st out of 279 journals in the category ''Pharmacology & Pharmacy'' and 35th out of 137 journals in the category ''Microbiology''. References External links * Delayed open access journals Pu ...
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Plasmodium Falciparum
''Plasmodium falciparum'' is a Unicellular organism, unicellular protozoan parasite of humans, and the deadliest species of ''Plasmodium'' that causes malaria in humans. The parasite is transmitted through the bite of a female ''Anopheles'' mosquito and causes the disease's most dangerous form, falciparum malaria. It is responsible for around 50% of all malaria cases. ''P. falciparum'' is therefore regarded as the deadliest parasite in humans. It is also associated with the development of blood cancer (Burkitt's lymphoma) and is classified as a List of IARC Group 2A carcinogens, Group 2A (probable) carcinogen. The species originated from the malarial parasite ''Laverania'' found in gorillas, around 10,000 years ago. Alphonse Laveran was the first to identify the parasite in 1880, and named it ''Oscillaria malariae''. Ronald Ross discovered its transmission by mosquito in 1897. Giovanni Battista Grassi elucidated the complete transmission from a female Anopheles, anopheline mosquit ...
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Shikimate Pathway
The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine). This pathway is not found in animal cells. The seven enzymes involved in the shikimate pathway are DAHP synthase, 3-dehydroquinate synthase, 3-dehydroquinate dehydratase, shikimate dehydrogenase, shikimate kinase, EPSP synthase, and chorismate synthase. The pathway starts with two substrates, phosphoenol pyruvate and erythrose-4-phosphate, and ends with chorismate, a substrate for the three aromatic amino acids. The fifth enzyme involved is the shikimate kinase, an enzyme that catalyzes the ATP-dependent phosphorylation of shikimate to form shikimate 3-phosphate (shown in the figure below). Shikimate 3-phosphate is then coupled with phosphoenol pyruvate to give 5-enolpyruvylshikimate-3-phosphate via the enzyme 5-enolpyruvylshikimate ...
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Chorismate Synthase
The enzyme chorismate synthase (EC 4.2.3.5) catalyzes the chemical reaction :5-''O''-(1-carboxyvinyl)-3-phosphoshikimate \rightleftharpoons chorismate + phosphate This enzyme belongs to the family of lyases, specifically those carbon-oxygen lyases acting on phosphates. The systematic name of this enzyme class is 5-''O''-(1-carboxyvinyl)-3-phosphoshikimate phosphate-lyase (chorismate-forming). This enzyme is also called 5-''O''-(1-carboxyvinyl)-3-phosphoshikimate phosphate-lyase. This enzyme participates in phenylalanine, tyrosine and tryptophan biosynthesis. Chorismate synthase catalyzes the last of the seven steps in the shikimate pathway which is used in prokaryotes, fungi and plants for the biosynthesis of aromatic amino acids. It catalyzes the 1,4-trans elimination of the phosphate group from 5-enolpyruvylshikimate-3-phosphate (EPSP) to form chorismate which can then be used in phenylalanine, tyrosine or tryptophan biosynthesis. Chorismate synthase requires the presenc ...
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4-aminobenzoic Acid
4-Aminobenzoic acid (also known as ''para''-aminobenzoic acid or PABA because the two functional groups are attached to the benzene ring across from one another in the ''para'' position) is an organic compound with the formula H2NC6H4CO2H. PABA is a white solid, although commercial samples can appear gray. It is slightly soluble in water. It consists of a benzene ring substituted with amino and carboxyl groups. The compound occurs extensively in the natural world. Production and occurrence In industry, PABA is prepared mainly by two routes: * Reduction of 4-nitrobenzoic acid * Hoffman degradation of the monoamide derived from terephthalic acid. Food sources of PABA include liver, brewer's yeast (and unfiltered beer), kidney, molasses, mushrooms, and whole grains. A review on this compound. Biology Biochemistry PABA is an intermediate in the synthesis of folate by bacteria, plants, and fungi. Many bacteria, including those found in the human intestinal tract such as ''E ...
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Journal Of Biological Chemistry
The ''Journal of Biological Chemistry'' (''JBC'') is a weekly peer-reviewed scientific journal that was established in 1905., jbc.org Since 1925, it is published by the American Society for Biochemistry and Molecular Biology. It covers research in areas of biochemistry and molecular biology. The editor is Alex Toker. As of January 2021, the journal is fully open access. In press articles are available free on its website immediately after acceptance. Editors The following individuals have served as editors of the journal: * 1906–1909: John Jacob Abel and Christian Archibald Herter * 1909–1910: Christian Archibald Herter * 1910–1914: Alfred Newton Richards * 1914–1925: Donald D. Van Slyke * 1925–1936: Stanley R. Benedict. After Benedict died, John T. Edsall served as temporary editor until the next editor was appointed. * 1937–1958: Rudolph J. Anderson * 1958–1967: John T. Edsall * 1968–1971: William Howard Stein * 1971–2011: Herbert Tabor * 2011–2015: ...
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Escherichia Coli
''Escherichia coli'' (),Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. also known as ''E. coli'' (), is a Gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escherichia'' that is commonly found in the lower intestine of warm-blooded organisms. Most ''E. coli'' strains are harmless, but some serotypes ( EPEC, ETEC etc.) can cause serious food poisoning in their hosts, and are occasionally responsible for food contamination incidents that prompt product recalls. Most strains do not cause disease in humans and are part of the normal microbiota of the gut; such strains are harmless or even beneficial to humans (although these strains tend to be less studied than the pathogenic ones). For example, some strains of ''E. coli'' benefit their hosts by producing vitamin K2 or by preventing the colonization of the intestine by pathogenic bacteria. These mutually beneficial relationships between ''E. col ...
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Shikimic Acid
Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower ''shikimi'' (, the Japanese star anise, ''Illicium anisatum''), from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later. Biosynthesis Phosphoenolpyruvate and erythrose-4-phosphate condense to form 3-deoxy-D-arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalyzed by the enzyme DAHP synthase. DAHP is then transformed to 3-dehydroquinate (DHQ), in a reaction catalyzed by DHQ synthase. Although this reaction requires nicotinamide adenine dinucleotide (NAD) as a cofactor, the enzymic mechanism regenerates it, resulting in the net use of no NAD. : DHQ is dehydrated to 3-dehydroshikimic acid by the enzyme 3-dehydroquinate dehydratase, which is reduced to shiki ...
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Antibiotics
An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of such infections. They may either kill or inhibit the growth of bacteria. A limited number of antibiotics also possess antiprotozoal activity. Antibiotics are not effective against viruses such as the common cold or influenza; drugs which inhibit viruses are termed antiviral drugs or antivirals rather than antibiotics. Sometimes, the term ''antibiotic''—literally "opposing life", from the Greek roots ἀντι ''anti'', "against" and βίος ''bios'', "life"—is broadly used to refer to any substance used against microbes, but in the usual medical usage, antibiotics (such as penicillin) are those produced naturally (by one microorganism fighting another), whereas non-antibiotic antibacterials (such as sulfonamides and antisep ...
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Fluorinated Carboxylic Acids
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens (F2, Cl2, Br2, I2). Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride. Organic chemistry Several pathways exist for the halogenation of organic compounds, including free radical halogenation, ketone halogenation, electrophilic halogenation, and halogen addition reaction. The nature of the substrate determines the pathway. The facility of halogenation is influenced by the halogen. Fluorine and chlorine are more electrophilic and a ...
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Cyclitols
In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is or where 3 ≤ ''x'' ≤ ''n''. The name is also used for compounds that can be viewed as result of substituting various functional groups for the hydrogen atoms in such a molecule, as well as similar molecules with one or more double bonds in the ring. Cyclitols and their derivatives are some of the compatible solutes which are formed in a plant as a response to salt or water stress. Some cyclitols (e.g. quinic or shikimic acid) are parts of hydrolysable tannins. Isomerism and nomenclature Unsubstituted cyclitols with the same ring size and number of hydroxyls may exist in several structural isomers, depending on the position of the hydroxyls along the ring. For example, cyclohexanetriol exists in three distinct isomers (1,2,3-, 1,2,4-, and 1,3,5-). Furthermore, the hydrogen and the hydroxyl ...
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