In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group (R−C=O) or hydrogen in the case of formyl group (H−C=O). In organic chemistry, the acyl group (IUPAC name alkanoyl if the organyl group is alkyl) is usually derived from a carboxylic acid, in which case it has the formula R−C(=O)−, where R represents an organyl group or hydrogen. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond.
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Acyl in the context of Ether lipid
In biochemistry, an ether lipid refers to any lipid in which the lipid "tail" group is attached to the glycerol backbone via an ether bond at any position. In contrast, conventional glycerophospholipids and triglycerides are triesters. Structural types include:
- Ether phospholipids: phospholipids are known to have ether-linked "tails" instead of the usual ester linkage.
- Ether on sn-1, ester on sn-2: "ether lipids" in the context of bacteria and eukaryotes refer to this class of lipids. Compared to the usual 1,2-diacyl-sn-glycerol (DAG), the sn-1 linkage is replaced with an ester bond.
Based on whether the sn-1 lipid is unsaturated next to the ether linkage, they can be further divided into alkenyl-acylphospholipids ("plasmenylphospholipid", 1-0-alk-1’-enyl-2-acyl-sn-glycerol) and alkyl-acylphospholipids ("plasmanylphospholipid"). This class of lipids have important roles in human cell signaling and structure.
Acyl in the context of Lamellar phase
Lamellar phase refers generally to packing of polar-headed, long chain, nonpolar-tailed molecules (amphiphiles) in an environment of bulk polar liquid, as sheets of bilayers separated by bulk liquid. In biophysics, polar lipids (mostly, phospholipids, and rarely, glycolipids) pack as a liquid crystalline bilayer, with hydrophobic fatty acyl long chains directed inwardly and polar headgroups of lipids aligned on the outside in contact with water, as a 2-dimensional flat sheet surface. Under transmission electron microscopy (TEM), after staining with polar headgroup reactive chemical osmium tetroxide, lamellar lipid phase appears as two thin parallel dark staining lines/sheets, constituted by aligned polar headgroups of lipids. 'Sandwiched' between these two parallel lines, there exists one thicker line/sheet of non-staining closely packed layer of long lipid fatty acyl chains. This TEM-appearance became famous as Robertson's unit membrane - the basis of all biological membranes, and structure of lipid bilayer in unilamellar liposomes. In multilamellar liposomes, many such lipid bilayer sheets are layered concentrically with water layers in between.
In lamellar lipid bilayers, polar headgroups of lipids align together at the interface of water and hydrophobic fatty-acid acyl chains align parallel to one another 'hiding away' from water. The lipid head groups are somewhat more 'tightly' packed than relatively 'fluid' hydrocarbon fatty acyl long chains. The lamellar lipid bilayer organization, thus reveals a 'flexibility gradient' of increasing freedom of motions from near the head-groups towards the terminal fatty-acyl chain methyl groups. Existence of such a dynamic organization of lamellar phase in liposomes as well as biological membranes can be confirmed by spin label electron paramagnetic resonance and high resolution nuclear magnetic resonance spectroscopy studies of biological membranes and liposomes.