Muramic Acid
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Muramic Acid
Muramic acid is an amino sugar acid. In terms of chemical composition, it is the ether of lactic acid and glucosamine. It occurs naturally as ''N''-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial 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, ...s. References Sugar acids Amino sugars {{amine-stub ...
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Sugar Acid
In organic chemistry, a sugar acid or acidic sugar is a monosaccharide with a carboxyl group at one end or both ends of its Polymer backbone, chain. Main classes of sugar acids include: * Aldonic acids, in which the aldehyde group () located at the initial end (Monosaccharide#Linear-chain monosaccharides, position 1) of an aldose is oxidized. * Ulosonic acids, in which the hydroxymethyl group () at the initial end of a 2-ketose is oxidized creating an α-ketoacid. * Uronic acids, in which the group at the terminal end of an aldose or ketose is oxidized. * Aldaric acids, in which both ends ( and ) of an aldose are oxidized. Examples Examples of sugar acids include: * Aldonic acids ** Glyceric acid (3C) ** Xylonic acid (5C) ** Gluconic acid (6C) ** Ascorbic acid (6C, unsaturated lactone) * Ulosonic acids ** Neuraminic acid (5-amino-3,5-dideoxy-D-glyceraldehyde, ''glycero''-D-galactose, ''galacto''-non-2-ulosonic acid) ** Ketodeoxyoctulosonic acid (KDO or 3-deoxy-D-mannose, ''mann ...
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Ether
In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin. Structure and bonding Ethers feature bent linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141  pm. The barrier to rotation about the C–O bonds is low. The bonding of ox ...
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Lactic Acid
Lactic acid is an organic acid. It has the molecular formula C3H6O3. It is white in the solid state and it is miscible with water. When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as natural sources. Lactic acid is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group. It is used as a synthetic intermediate in many organic synthesis industries and in various biochemical industries. The conjugate base of lactic acid is called lactate (or the lactate anion). The name of the derived acyl group is lactoyl. In solution, it can ionize by a loss of a proton to produce the lactate ion . Compared to acetic acid, its p''K'' is 1 unit less, meaning lactic acid is ten times more acidic than acetic acid. This higher acidity is the consequence of the intramolecular hydrogen bonding between the α-hydroxyl and the carboxylate group. Lactic acid is chiral, consisting of two en ...
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Glucosamine
Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country. Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug in the United States. Dietary supplement Oral glucosamine is a dietary supplement and is not a prescription drug in the United States. Glucosamine is marketed as a supplement to support the structure and function of joints, and the marketing is targeted to people with osteoarthritis. Commonly sold forms of glucosamine are glucosamine sulfate, glucosamine chondroitin, glu ...
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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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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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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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PubChem
PubChem is a database of Chemistry, chemical molecules and their activities against biological assays. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH). PubChem can be accessed for free through a web user interface. Millions of compound structures and descriptive datasets can be freely downloaded via FTP. PubChem contains multiple substance descriptions and small molecules with fewer than 100 atoms and 1,000 bonds. More than 80 database vendors contribute to the growing PubChem database. History PubChem was released in 2004 as a component of the Molecular Libraries Program (MLP) of the NIH. As of November 2015, PubChem contains more than 150 million depositor-provided substance descriptions, 60 million unique chemical structures, and 225 million biological activity test results (from over 1 million assay experiments performe ...
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Sugar Acids
In organic chemistry, a sugar acid or acidic sugar is a monosaccharide with a carboxyl group at one end or both ends of its chain. Main classes of sugar acids include: * Aldonic acids, in which the aldehyde group () located at the initial end ( position 1) of an aldose is oxidized. * Ulosonic acids, in which the hydroxymethyl group () at the initial end of a 2-ketose is oxidized creating an α-ketoacid. * Uronic acids, in which the group at the terminal end of an aldose or ketose is oxidized. * Aldaric acids, in which both ends ( and ) of an aldose are oxidized. Examples Examples of sugar acids include: * Aldonic acids ** Glyceric acid (3C) ** Xylonic acid (5C) ** Gluconic acid (6C) ** Ascorbic acid (6C, unsaturated lactone) * Ulosonic acids ** Neuraminic acid (5-amino-3,5-dideoxy-D- ''glycero''-D- ''galacto''-non-2-ulosonic acid) ** Ketodeoxyoctulosonic acid (KDO or 3-deoxy-D- ''manno''-oct-2-ulosonic acid) * Uronic acids ** Glucuronic acid (6C) ** Galacturonic acid (6C) ...
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