Saccharolipid

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Chemical structure of lipid A as found in E. Coli Lipid A.png
Chemical structure of lipid A as found in E. Coli

Saccharolipids are chemical compounds containing fatty acids linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a monosaccharide substitutes for the glycerol backbone present in glycerolipids and glycerophospholipids. The most familiar saccharolipids are the acylated glucosamine precursors of the lipid A component of the lipopolysaccharides in Gram-negative bacteria. Typical lipid A molecules are disaccharides of glucosamine, which are derivatized with as many as seven fatty-acyl chains. The minimal lipopolysaccharide required for growth in Escherichia coli is Kdo2-Lipid A, a hexa-acylated disaccharide of glucosamine (LipidA) that is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo) residues. [2]

Acyl-trehaloses, such as Mycobacterial cord factor are further examples of sacharolipids.

While terms are sometimes used interchangeably, Saccharolipids are distinct from glycolipids as the latter are defined by IUPAC to have the sugar bound by a glycosidic linkage to a fatty acyl. [3] The LIPID MAPS classification system also defines saccharolipids as a distinct category of lipids. [4]

See also

Related Research Articles

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<span class="mw-page-title-main">Glycolipid</span> Class of chemical compounds

Glycolipids are lipids with a carbohydrate attached by a glycosidic (covalent) bond. Their role is to maintain the stability of the cell membrane and to facilitate cellular recognition, which is crucial to the immune response and in the connections that allow cells to connect to one another to form tissues. Glycolipids are found on the surface of all eukaryotic cell membranes, where they extend from the phospholipid bilayer into the extracellular environment.

<span class="mw-page-title-main">Sphingolipid</span> Family of chemical compounds

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<span class="mw-page-title-main">Lipid A</span>

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<span class="mw-page-title-main">Glycerophospholipid</span> Class of lipids

Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes. Two major classes are known: those for bacteria and eukaryotes and a separate family for archaea.

<span class="mw-page-title-main">Bacterial outer membrane</span>

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<span class="mw-page-title-main">ACOT2</span> Protein-coding gene in the species Homo sapiens

Acyl-CoA thioesterase 2, also known as ACOT2, is an enzyme which in humans is encoded by the ACOT2 gene.

<span class="mw-page-title-main">ACOT4</span> Protein-coding gene in the species Homo sapiens

Acyl-coenzyme A thioesterase 4 is an enzyme that in humans is encoded by the ACOT4 gene.

<span class="mw-page-title-main">ACOT11</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">ACSF3</span> Protein-coding gene in the species Homo sapiens

Acyl-CoA synthetase family member 3 is an enzyme that in humans is encoded by the ACSF3 gene.

In molecular biology, the lipopolysaccharide kinase (Kdo/WaaP) family is a family of kinases.

UDP-3-O-(3-hydroxymyristoyl)glucosamine N-acyltransferase is an enzyme with systematic name (3R)-3-hydroxymyristoyl-(acyl-carrier protein):UDP-3-O-( -3-hydroxymyristoyl)-alpha-D-glucosamine N-acetyltransferase. This enzyme catalyses the following chemical reaction

Lipid IVA 3-deoxy-D-manno-octulosonic acid transferase is an enzyme with systematic name CMP-3-deoxy-D-manno-oct-2-ulosonate:lipid IVA 3-deoxy-D-manno-oct-2-ulosonate transferase. This enzyme catalyses the following chemical reaction

(KDO)-lipid IVA 3-deoxy-D-manno-octulosonic acid transferase is an enzyme with systematic name CMP-3-deoxy-D-manno-oct-2-ulosonate:(KDO)-lipid IVA 3-deoxy-D-manno-oct-2-ulosonate transferase. This enzyme catalyses the following chemical reaction

3-deoxy-D-manno-octulosonic acid kinase is an enzyme with systematic name ATP:(KDO)-lipid IVA 3-deoxy-alpha-D-manno-oct-2-ulopyranose 4-phosphotransferase. This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">ACOT1</span> Protein-coding gene in the species Homo sapiens

Acyl-CoA thioesterase 1 is a protein that in humans is encoded by the ACOT1 gene.

<span class="mw-page-title-main">ACSS3</span> Protein-coding gene in the species Homo sapiens

Acyl-CoA synthetase short-chain family member 3 is a protein that in humans is encoded by the ACSS3 gene.

References

  1. Raetz, Christian R. H.; Guan, Ziqiang; Ingram, Brian O.; Six, David A.; Song, Feng; Wang, Xiaoyuan; Zhao, Jinshi (2009). "Discovery of new biosynthetic pathways: the lipid A story". Journal of Lipid Research. 50 Suppl: S103–S108. doi:10.1194/jlr.R800060-JLR200. PMC   2674688 . PMID   18974037.
  2. Raetz CR; Garrett TA; Reynolds CM; Shaw WA; Moore JD; Smith DC Jr; Ribeiro AA; Murphy RC; Ulevitch RJ; Fearns C; Reichart D; Glass CK; Benner C; Subramaniam S; Harkewicz R; Bowers-Gentry RC; Buczynski MW; Cooper JA; Deems RA; Dennis EA (2006). "Kdo2-Lipid A of Escherichia coli, a defined endotoxin that activates macrophages via TLR-4". Journal of Lipid Research. 47 (5): 1097–1111. doi: 10.1194/jlr.M600027-JLR200 . PMID   16479018.
  3. "Nomenclature of Glycolipids (IUPAC Recommendations 1997)". Pure and Applied Chemistry. 69: 2475–2487. 1997. doi: 10.1351/pac199769122475 .
  4. "A comprehensive classification system for lipids" (PDF). Journal of Lipid Research. 46: 839–861. 2005. doi:10.1194/jlr.E400004-JLR200. PMID   15722563.