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Glycerophospholipid
Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes in eukaryotic cells. They are a type of lipid, of which its composition affects membrane structure and properties. Two major classes are known: those for bacteria and eukaryotes and a separate family for archaea. Structures Glycerophospholipids are derived from glycerol-3-phosphate in a de novo pathway. The term glycerophospholipid signifies any derivative of glycerophosphoric acid that contains at least one ''O''- acyl, or ''O''-alkyl, or ''O''-alk-1'-enyl residue attached to the glycerol moiety. The phosphate group forms an ester linkage to the glycerol. The long-chained hydrocarbons are typically attached through ester linkages in bacteria/eukaryotes and by ether linkages in archaea. In bacteria and procaryotes, the lipids consist of diesters commonly of C16 or C18 fatty acids. These acids are straight-chained and, especially for the C18 membe ...
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Lipid
Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology. Lipids are broadly defined as hydrophobic or amphiphilic small molecules; the amphiphilic nature of some lipids allows them to form structures such as vesicles, multilamellar/ unilamellar liposomes, or membranes in an aqueous environment. Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building-blocks": ketoacyl and isoprene groups. Using this approach, lipids may be divided into eight categories: fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, saccharolipids, and polyketides (derived from condensatio ...
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Plasmalogen
Plasmalogens are a class of glycerophospholipid with a plasmenyl group linked to a lipid at the sn-1 position of the glycerol backbone. Plasmalogens are found in multiple domains of life, including Mammal, mammals, Invertebrate, invertebrates, protozoa, and Anaerobic organism, anaerobic bacteria. They are commonly found in cell membranes in the nervous system, nervous, immune system, immune, and cardiovascular systems. In humans, lower levels of plasmalogens are studied in relation to some diseases. Plasmalogens are also associated with adaptations to extreme environments in non-human organisms. Structure Glycerophospholipids of biochemical relevance are divided into three subclasses based on the substitution present at the Glycerophospholipid#Nomenclature and stereochemistry, sn-1 position of the glycerol backbone: acyl_group, acyl, alkyl_group, alkyl and alkenyl_group, alkenyl. Of these, the alkyl and alkenyl moiety in each case form an ether bond, which makes for two types o ...
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Glycerol 3-phosphate
''sn''-Glycerol 3-phosphate is the organic ion with the formula HOCH2CH(OH)CH2OPO32-. It is one of two stereoisomers of the ester of dibasic phosphoric acid (HOPO32-) and glycerol. It is a component of bacterial and eukaryotic glycerophospholipids. From a historical reason, it is also known as -glycerol 3-phosphate, -glycerol 1-phosphate, -α-glycerophosphoric acid. Biosynthesis Glycerol 3-phosphate is synthesized by reducing dihydroxyacetone phosphate (DHAP), an intermediate in glycolysis. The reduction is catalyzed by glycerol-3-phosphate dehydrogenase. DHAP and thus glycerol 3-phosphate can also be synthesized from amino acids and citric acid cycle intermediates via the glyceroneogenesis pathway. : + NAD(P)H + H+ → + NAD(P)+ It is also synthesized by the phosphorylation of glycerol, which is generated by hydrolysis of fats. This esterification is catalyzed by glycerol kinase. : + ATP → + ADP Metabolism and biological function Glycerol 3-phosphate is a start ...
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Glycerol
Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pharmaceutical formulations. Because of its three hydroxyl groups, glycerol is miscible with water and is Hygroscopy, hygroscopic in nature. Modern use of the word glycerine (alternatively spelled glycerin) refers to commercial preparations of less than 100% purity, typically 95% glycerol. Structure Although chirality, achiral, glycerol is prochirality, prochiral with respect to reactions of one of the two primary alcohols. Thus, in substituted derivatives, the Glycerophospholipid#Nomenclature and stereochemistry, stereospecific numbering labels the molecule with a ''sn''- prefix before the stem name of the molecule. Production Natural sources Glycerol is generally obtained from plant and animal sources where it occurs in triglycerides, est ...
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Phospholipid
Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typically have omega-3 fatty acids EPA and DHA integrated as part of the phospholipid molecule. The phosphate group can be modified with simple organic molecules such as choline, ethanolamine or serine. Phospholipids are a key component of all cell membranes. They can form lipid bilayers because of their amphiphilic characteristic. In eukaryotes, cell membranes also contain another class of lipid, sterol, interspersed among the phospholipids. The combination provides fluidity in two dimensions combined with mechanical strength against rupture. Purified phospholipids are produced commercially and have found applications in nanotechnology and materials science. The first phospholipid identified in 1847 as such in biological tissues w ...
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Phosphatidate
Phosphatidic acids are anionic phospholipids important to cell signaling and direct activation of lipid-gated ion channels. Hydrolysis of phosphatidic acid gives rise to one molecule each of glycerol and phosphoric acid and two molecules of fatty acids. They constitute about 0.25% of phospholipids in the bilayer. Structure Phosphatidic acid consists of a glycerol backbone, with, in general, a saturated fatty acid bonded to carbon-1, an unsaturated fatty acid bonded to carbon-2, and a phosphate group bonded to carbon-3. Formation and degradation Besides de novo synthesis, PA can be formed in three ways: * By phospholipase D (PLD), via the hydrolysis of the P-O bond of phosphatidylcholine (PC) to produce PA and choline. * By the phosphorylation of diacylglycerol (DAG) by DAG kinase (DAGK). * By the acylation of lysophosphatidic acid by lysoPA-acyltransferase (LPAAT); this is the most common pathway.Devlin, T. M. 2004. ''Bioquímica'', 4ª edición. Reverté, Barcelona. The glyc ...
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Phosphatidylcholine
Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can easily be obtained from a variety of readily available sources, such as egg yolk or soybeans, from which they are mechanically or chemically extracted using hexane. They are also a member of the lecithin group of yellow-brownish fatty substances occurring in animal and plant tissues. Dipalmitoylphosphatidylcholine (lecithin) is a major component of the pulmonary surfactant, and is often used in the lecithin–sphingomyelin ratio to calculate fetal lung maturity. While phosphatidylcholines are found in all plant and animal cells, they are absent in the membranes of most bacteria, including ''Escherichia coli ''Escherichia coli'' ( )Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. is a gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus '' Esch ...
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Lecithin
Lecithin ( ; from the Ancient Greek "yolk") is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are amphiphilic – they attract both water and fatty substances (and so are both hydrophilic and lipophilic), and are used for smoothing food textures, emulsifying, homogenizing liquid mixtures, and repelling sticking materials. Lecithins are mixtures of glycerophospholipids including phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid. Lecithin was first isolated in 1845 by the French chemist and pharmacist Théodore Gobley. In 1850, he named the phosphatidylcholine . Gobley originally isolated lecithin from egg yolk and established the complete chemical formula of phosphatidylcholine in 1874; in between, he demonstrated the presence of lecithin in a variety of biological materials, including venous blood, human lungs, bile, roe, and brains of ...
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Phosphatidylinositol
Phosphatidylinositol or inositol phospholipid is a biomolecule. It was initially called "inosite" when it was discovered by Léon Maquenne and Johann Joseph von Scherer in the late 19th century. It was discovered in bacteria but later also found in eukaryotes, and was found to be a signaling molecule. The biomolecule can exist in 9 different isomers. It is a lipid which contains a phosphate group, two fatty acid chains, and one inositol sugar molecule. Typically, the phosphate group has a negative charge (at physiological pH values). As a result, the molecule is amphiphilic. The production of the molecule is limited to the endoplasmic reticulum. History of phospatidylinositol Phosphatidylinositol (PI) and its derivatives have a rich history dating back to their discovery by Johann Joseph von Scherer and Léon Maquenne in the late 19th century. Initially known as " inosite" based on its sweet taste, the isolation and characterization of inositol laid the groundwork for und ...
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Archaea Membrane
Archaea ( ) is a domain of organisms. Traditionally, Archaea only included its prokaryotic members, but this has since been found to be paraphyletic, as eukaryotes are known to have evolved from archaea. Even though the domain Archaea cladistically includes eukaryotes, the term "archaea" (: archaeon , from the Greek "ἀρχαῖον", which means ancient) in English still generally refers specifically to prokaryotic members of Archaea. Archaea were initially classified as bacteria, receiving the name archaebacteria (, in the Archaebacteria kingdom), but this term has fallen out of use. Archaeal cells have unique properties separating them from Bacteria and Eukaryota. Archaea are further divided into multiple recognized phyla. Classification is difficult because most have not been isolated in a laboratory and have been detected only by their gene sequences in environmental samples. It is unknown if they can produce endospores. Archaea are often similar to bacteria in siz ...
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Cytosol
The cytosol, also known as cytoplasmic matrix or groundplasm, is one of the liquids found inside cells ( intracellular fluid (ICF)). It is separated into compartments by membranes. For example, the mitochondrial matrix separates the mitochondrion into many compartments. In the eukaryotic cell, the cytosol is surrounded by the cell membrane and is part of the cytoplasm, which also comprises the mitochondria, plastids, and other organelles (but not their internal fluids and structures); the cell nucleus is separate. The cytosol is thus a liquid matrix around the organelles. In prokaryotes, most of the chemical reactions of metabolism take place in the cytosol, while a few take place in membranes or in the periplasmic space. In eukaryotes, while many metabolic pathways still occur in the cytosol, others take place within organelles. The cytosol is a complex mixture of substances dissolved in water. Although water forms the large majority of the cytosol, its structure and proper ...
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Enantiomer
In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities which are mirror images of each other and non-superposable. Enantiomer molecules are like right and left hands: one cannot be superposed onto the other without first being converted to its mirror image. It is solely a relationship of chirality (chemistry), chirality and the permanent three-dimensional relationships among molecules or other chemical structures: no amount of re-orientation of a molecule as a whole or conformational isomerism, conformational change converts one chemical into its enantiomer. Chemical structures with chirality rotate plane-polarized light. A mixture of equal amounts of each enantiomer, a ''racemic mixture'' or a ''racemate'', does not rotate light. Stereoisomers include both enantiomers and diastereomers. Diaste ...
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