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Phosphatidylinositol (or Inositol Phospholipid) consists of a family of lipids as illustrated on the right, where red is x, blue is y, and black is z, in the context of independent variation, a class of the phosphatidylglycerides. In such molecules the isomer of the
inositol Inositol, or more precisely ''myo''-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and ...
group is assumed to be the myo- conformer unless otherwise stated. Typically phosphatidylinositols form a minor component on the cytosolic side of eukaryotic
cell membranes The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of all cells from the outside environment ( ...
. The phosphate group gives the molecules a negative charge at physiological pH. The form of phosphatidylinositol comprising the isomer ''muco''-inositol acts as a sensory receptor in the taste function of the sensory system. In this context it is often referred to as PtdIns, but that does not imply any molecular difference from phosphatidylinositols comprising the myo- conformers of inositol. The phosphatidylinositol can be phosphorylated to form phosphatidylinositol phosphate (PI-4-P, referred to as PIP in close context or informally), phosphatidylinositol bisphosphate (PIP2) and phosphatidylinositol trisphosphate (PIP3). All lipids based on phosphatidylinositol are known as inositides, or sometimes phosphoinositides.


Biosynthesis

The synthesis of phosphatidylinositol in the laboratory is catalyzed by phosphatidylinositol synthase and involves CDP-diacylglycerol and L-''myo''-inositol.


Chemistry

PI has a polar and non-polar region, making the lipid an
amphiphile An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'') properties. Such a compoun ...
. Phosphatidylinositol is classified as a glycerophospholipid that contains a glycerol backbone, two non-polar fatty acid tails, a phosphate group substituted with an
inositol Inositol, or more precisely ''myo''-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and ...
polar head group. The most common fatty acids of phosphoinositides are
stearic acid Stearic acid ( , ) is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "''stéar''", which means tallow. ...
in the SN1 position and
arachidonic acid Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6), or 20:4(5,8,11,14). It is structurally related to the saturated arachidic acid found in cupuaçu butter. Its name derives from the New Latin word ''arachi ...
, in the SN2 position. Hydrolysis of phosphoinositides yield one mole of glycerol, two moles of fatty acids, one mole of inositol and one, two, or three moles of phosphoric acids, depending on the number of phosphates on the inositol rings. Phosphoinositides are regarded as the most acidic phospholipids. The specific fatty acids of PtdIns, and their conformation, employed in the sensory neurons has not been elucidated.


Phosphoinositides

Phosphorylated forms of phosphatidylinositol (PI) are called phosphoinositides and play important roles in
lipid signaling Lipid signaling, broadly defined, refers to any biological signaling event involving a lipid messenger that binds a protein target, such as a receptor, kinase or phosphatase, which in turn mediate the effects of these lipids on specific cellular r ...
, cell signaling and membrane trafficking. The inositol ring can be phosphorylated by a variety of kinases on the three, four and five hydroxyl groups in seven different combinations. However, the two and six hydroxyl groups are typically not phosphorylated due to steric hindrance. All seven variations of the following phosphoinositides have been found in animals: Phosphatidylinositol monophosphates: * Phosphatidylinositol 3-phosphate, also known as PtdIns3''P'' or PI(3)P *
Phosphatidylinositol 4-phosphate Phosphatidylinositol-4-phosphate (PtdIns4''P'', PI-4-P, PI4P, or PIP) is a precursor of phosphatidylinositol (4,5)-bisphosphate. PtdIns4''P'' is prevalent in the membrane of the Golgi apparatus. In the Golgi apparatus, PtdIns4''P'' binds to the GT ...
, also known as PtdIns4''P'' or PI(4)P *
Phosphatidylinositol 5-phosphate Phosphatidylinositol 5-phosphate (PtdIns5P) is a phosphoinositide, one of the phosphorylated derivatives of phosphatidylinositol (PtdIns), that are well-established membrane-anchored regulatory molecules. Phosphoinositides participate in signaling ...
, also known as PtdIns5''P'' or PI(5)P Phosphatidylinositol bisphosphates: *
Phosphatidylinositol 3,4-bisphosphate Phosphatidylinositol (3,4)-bisphosphate (PtdIns(3,4)''P''2) is a minor phospholipid component of cell membranes, yet an important second messenger. The generation of PtdIns(3,4)''P''2 at the plasma membrane activates a number of important cell sig ...
, also known as PtdIns(3,4)''P''2 or PI(3,4)P2 *
Phosphatidylinositol 3,5-bisphosphate Phosphatidylinositol 3,5-bisphosphate (PtdIns(3,5)P2) is one of the seven phosphoinositides found in eukaryotic cell membranes. In quiescent cells, the PtdIns(3,5)P2 levels, typically quantified by HPLC, are the lowest amongst the constitutively pr ...
, also known as PtdIns(3,5)''P''2 or PI(3,5)P2 * Phosphatidylinositol 4,5-bisphosphate, also known as PtdIns(4,5)''P''2, PI(4,5)P2 or often simply referred to as PIP2 Phosphatidylinositol trisphosphate: * Phosphatidylinositol 3,4,5-trisphosphate, also known as PtdIns(3,4,5)''P''3 or PI(3,4,5)P3 These phosphoinositides are also found in plant cells, with the exception of PIP3.


See also

*
PI 3-kinase Phosphoinositide 3-kinases (PI3Ks), also called phosphatidylinositol 3-kinases, are a family of enzymes involved in cellular functions such as cell growth, proliferation, differentiation, motility, survival and intracellular trafficking, which i ...
* Inositol phosphate * Phosphatidylinositol 3-phosphate *
Phosphatidylinositol 4-phosphate Phosphatidylinositol-4-phosphate (PtdIns4''P'', PI-4-P, PI4P, or PIP) is a precursor of phosphatidylinositol (4,5)-bisphosphate. PtdIns4''P'' is prevalent in the membrane of the Golgi apparatus. In the Golgi apparatus, PtdIns4''P'' binds to the GT ...
*
Phosphatidylinositol 5-phosphate Phosphatidylinositol 5-phosphate (PtdIns5P) is a phosphoinositide, one of the phosphorylated derivatives of phosphatidylinositol (PtdIns), that are well-established membrane-anchored regulatory molecules. Phosphoinositides participate in signaling ...
*
Phosphatidylinositol (3,4)-bisphosphate Phosphatidylinositol (3,4)-bisphosphate (PtdIns(3,4)''P''2) is a minor phospholipid component of cell membranes, yet an important second messenger. The generation of PtdIns(3,4)''P''2 at the plasma membrane activates a number of important cell sig ...
*
Phosphatidylinositol (3,5)-bisphosphate Phosphatidylinositol 3,5-bisphosphate (PtdIns(3,5)P2) is one of the seven phosphoinositides found in eukaryotic cell membranes. In quiescent cells, the PtdIns(3,5)P2 levels, typically quantified by HPLC, are the lowest amongst the constitutively p ...
* Phosphatidylinositol (4,5)-bisphosphate *
Inositol 1,4,5-triphosphate Inositol trisphosphate or inositol 1,4,5-trisphosphate abbreviated InsP3 or Ins3P or IP3 is an inositol phosphate signaling molecule. It is made by hydrolysis of phosphatidylinositol 4,5-bisphosphate (PIP2), a phospholipid that is located in the ...
*
Phosphatidylinositol (3,4,5)-trisphosphate Phosphatidylinositol (3,4,5)-trisphosphate (PtdIns(3,4,5)''P''3), abbreviated PIP3, is the product of the class I phosphoinositide 3-kinases (PI 3-kinases) phosphorylation of phosphatidylinositol (4,5)-bisphosphate (PIP2). It is a phospholipid th ...
* inositol pentakisphosphate * inositol hexaphosphate *
inositol triphosphate receptor Inositol trisphosphate receptor (InsP3R) is a membrane glycoprotein complex acting as a Ca2+ channel activated by inositol trisphosphate (InsP3). InsP3R is very diverse among organisms, and is necessary for the control of cellular and physio ...


References


Additional images

Image:Membrane_Lipids.svg, Membrane lipids Image:Phosphatidylinositol_core_skeletal.svg, Phosphatidyl-inositol Image:Myo-inositol structure.svg,
Inositol Inositol, or more precisely ''myo''-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and ...
Image:Glycerine chemical structure.png, Glycerol


External links

*
Phosphatidylinositol at Lipid Library
{{Phospholipids Phospholipids Membrane biology