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Diaminopimelate Pathway
Diaminopimelic acid (DAP) is an amino acid, representing an epsilon-carboxy derivative of lysine. ''meso''-α,ε-Diaminopimelic acid is the last intermediate in the biosynthesis of lysine and undergoes decarboxylation by diaminopimelate decarboxylase to give the final product. DAP is a characteristic of certain cell walls of some bacteria. DAP is often found in the peptide linkages of NAM- NAG chains that make up the cell wall of gram-negative bacteria. When provided, they exhibit normal growth. When in deficiency, they still grow but with the inability to make new cell wall peptidoglycan. This is also the attachment point for Braun's lipoprotein. See also * Aspartate-semialdehyde dehydrogenase, an enzyme involved in DAP synthesis * Peptidoglycan * Pimelic acid Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Pimelic acid is one unit longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. However compared ...
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Amino Acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 appear in the genetic code of life. Amino acids can be classified according to the locations of the core structural functional groups ( alpha- , beta- , gamma- amino acids, etc.); other categories relate to polarity, ionization, and side-chain group type ( aliphatic, acyclic, aromatic, polar, etc.). In the form of proteins, amino-acid '' residues'' form the second-largest component (water being the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis. It is thought that they played a key role in enabling life on Earth and its emergence. Amino acids are formally named by the IUPAC- IUBMB Joint Commi ...
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Gram-negative Bacteria
Gram-negative bacteria are bacteria that, unlike gram-positive bacteria, do not retain the Crystal violet, crystal violet stain used in the Gram staining method of bacterial differentiation. Their defining characteristic is that their cell envelope consists of a thin peptidoglycan gram-negative cell wall, cell wall sandwiched between an inner (Cytoplasm, cytoplasmic) Cell membrane, membrane and an Bacterial outer membrane, outer membrane. These bacteria are found in all environments that support life on Earth. Within this category, notable species include the model organism ''Escherichia coli'', along with various pathogenic bacteria, such as ''Pseudomonas aeruginosa'', ''Chlamydia trachomatis'', and ''Yersinia pestis''. They pose significant challenges in the medical field due to their outer membrane, which acts as a protective barrier against numerous Antibiotic, antibiotics (including penicillin), Detergent, detergents that would normally damage the inner cell membrane, and the ...
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Alpha-Amino Acids
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 appear in the genetic code of life. Amino acids can be classified according to the locations of the core structural functional groups ( alpha- , beta- , gamma- amino acids, etc.); other categories relate to polarity, ionization, and side-chain group type ( aliphatic, acyclic, aromatic, polar, etc.). In the form of proteins, amino-acid '' residues'' form the second-largest component (water being the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis. It is thought that they played a key role in enabling life on Earth and its emergence. Amino acids are formally named by the IUPAC- IUBMB Joint Commiss ...
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Pimelic Acid
Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Pimelic acid is one unit longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. However compared to adipic acid, pimelic acid is relatively small in importance industrially. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid lysine and the vitamin biotin. Synthesis Biosynthesis The biosynthesis of pimelic acid is unknown but is speculated to start with malonyl CoA. Chemical and industrial routes Like other simple dicarboxylic acids, many methods have been developed for producing pimelic acid. Pimelic acid is produced commercially by oxidation of cycloheptanone with dinitrogen tetroxide. Other routes include the relatively unselective oxidation of palmitic acid and the carbonylation of caprolactone. Niche methods Many other methods exist. Pimelic acid has been synthesized from cyclohexanone and from salicylic acid. In the former ...
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Peptidoglycan
Peptidoglycan or murein is a unique large macromolecule, a polysaccharide, consisting of sugars and amino acids that forms a mesh-like layer (sacculus) that surrounds the bacterial cytoplasmic membrane. The sugar component consists of alternating residues of β-(1,4) linked N-Acetylglucosamine, ''N''-acetylglucosamine (NAG) and N-Acetylmuramic acid, ''N''-acetylmuramic acid (NAM). Attached to the ''N''-acetylmuramic acid is an oligopeptide chain made of three to five amino acids. The peptide chain can be cross-linked to the peptide chain of another strand forming the 3D mesh-like layer. Peptidoglycan serves a structural role in the bacterial cell wall, giving structural strength, as well as counteracting the osmotic pressure of the cytoplasm. This repetitive linking results in a dense peptidoglycan layer which is critical for maintaining cell form and withstanding high osmotic pressures, and it is regularly replaced by peptidoglycan production. Peptidoglycan hydrolysis and synthesis ...
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Aspartate-semialdehyde Dehydrogenase
In enzymology, an aspartate-semialdehyde dehydrogenase () is an enzyme that is very important in the biosynthesis of amino acids in prokaryotes, fungi, and some higher plants. It forms an early branch point in the metabolic pathway forming lysine, methionine, leucine and isoleucine from aspartate. This pathway also produces diaminopimelate which plays an essential role in bacterial cell wall formation. There is particular interest in ASADH as disabling this enzyme proves fatal to the organism giving rise to the possibility of a new class of antibiotics, fungicides, and herbicides aimed at inhibiting it. The enzyme catalyzes the reversible chemical reaction :L-aspartate 4-semialdehyde + phosphate + NADP+ \rightleftharpoons L-4-aspartyl phosphate + NADPH + H+ The 3 substrates of this enzyme are L-aspartate 4-semialdehyde, phosphate, and NADP+, whereas its 3 products are L-4-aspartyl phosphate, NADPH, and H+. However, under physiological conditions the reaction runs in the ...
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Braun's Lipoprotein
Braun's lipoprotein (BLP, Lpp, murein lipoprotein, or major outer membrane lipoprotein) was first identified by V. Braun and K. Rehn in 1969, it was the first Lipoprotein identified prompting much further study in this area. It is found in some gram-negative cell walls, is one of the most abundant membrane proteins; its molecular weight is about 7.2 kDa. It is bound at its C-terminal end (a lysine) by a covalent bond to the peptidoglycan layer (specifically to diaminopimelic acid molecules) and is embedded in the outer membrane by its hydrophobic head (a cysteine with lipids attached). BLP tightly links the two layers and provides structural integrity to the outer membrane. Characteristics The gene encoding Braun's lipoprotein initially produces a protein composed of 78 amino acids, which includes a 20 amino acid signal peptide at the amino terminus. The mature protein is 6 kDa in size. Three monomers of Lpp assemble into a leucine zipper coiled-coil trimer. Large amounts ...
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Alpha And Beta Carbon
In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule. Numeric locants The International Union of Pure and Applied Chemistry (IUPAC) recommends the use of numeric prefixes to indicate the position of substituents, generally by identifying the parent hydrocarbon chain and assigning the carbon atoms based on their substituents in order of precedence. For example, there are at least two isomers of the linear form of pentanone, a ketone that contains a chain of exactly five carbon atoms. There is an oxygen atom bonded to one of the middle three carbons (if it were bonded to an end carbon, the molecule would be an aldehyde, not a ketone), but it is not clear where it is located. In this example, the carbon atoms are numbered from one to five, which starts at one end and proceeds sequentially along the chain. Now the position of the oxygen atom can be defined as on carbon atom number two, three o ...
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N-Acetylmuramic Acid
''N''-Acetylmuramic acid (NAM or MurNAc) is an organic compound with the chemical formula . It is a monomer of peptidoglycan in most bacterial cell walls, which is built from alternating units of ''N''-acetylglucosamine (GlcNAc) and ''N''-acetylmuramic acid, cross-linked by oligopeptides at the lactic acid residue of MurNAc. Formation of NAM NAM is an addition product of phosphoenolpyruvate and ''N''-acetylglucosamine. This addition happens exclusively in the cell cytoplasm. Clinical significance ''N''-Acetylmuramic acid (MurNAc) is part of the peptidoglycan polymer of bacterial cell walls. MurNAc is covalently linked to ''N''-acetylglucosamine and may also be linked through the hydroxyl on carbon number 4 to the carbon of L-alanine. A pentapeptide composed of L-alanyl-D-isoglutaminyl-L-lysyl-D-alanyl-D-alanine is added to the MurNAc in the process of making the peptidoglycan strands of the cell wall. Synthesis of NAM is inhibited by fosfomycin. NAG and NAM cross-linking ...
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Cell Wall
A cell wall is a structural layer that surrounds some Cell type, cell types, found immediately outside the cell membrane. It can be tough, flexible, and sometimes rigid. Primarily, it provides the cell with structural support, shape, protection, and functions as a selective barrier. Another vital role of the cell wall is to help the cell withstand osmotic pressure and mechanical stress. While absent in many eukaryotes, including animals, cell walls are prevalent in other organisms such as fungi, algae and plants, and are commonly found in most Prokaryote, prokaryotes, with the exception of Mollicutes, mollicute bacteria. The composition of cell walls varies across taxonomic groups, species, cell type, and the cell cycle. In Embryophyte, land plants, the primary cell wall comprises Polysaccharide, polysaccharides like cellulose, hemicelluloses, and pectin. Often, other Polymer, polymers such as lignin, suberin or cutin are anchored to or embedded in plant cell walls. Algae exhibit ...
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