Glycolipids Synthesis

Glycolipids are found in unicellular organisms as well as in complex organisms, attached to the phospholipid bilayer. These lipids extend from the phospholipid bilayer to the extracellular portion. Glycolipids are formed when a carbohydrate moiety combines with a monolipid or fatty acid moiety. BOC Sciences provides synthesis services for a wide range of glycolipids, including sphingolipids and glycerolipids, as well as quality analysis and structural characterization of prepared glycolipids to help our customers obtain high-quality products.

Fig 1. Synthesis of glycolipids. (Velasco-Torrijos et al., 2012)

Structure of Glycolipids

The basic structure of glycolipids consists of a monosaccharide group or oligosaccharide group attached to a sphingolipid or glycerol group (which can be acetylated or alkylated) and one or two fatty acids. They constitute the sphingolipid and glycerolipid classes, respectively. Glycolipids are anchored to the surface of the plasma membrane through hydrophobic interactions in the lipid tail and binding to the lipid bilayer. Glycolipids not only play a structural role in maintaining membrane stability, but also facilitate intercellular communication by acting as receptors, protein anchors, and regulators of signal transduction. They also have an amphiphilic structure, making them an important class of non-toxic, odorless, and readily biodegradable non-ionic biosurfactants.

Fig 2. Glycolipids in cell membrane.

Sphingolipid Synthesis Services from BOC Sciences

• Synthesis of sphingolipids

Sphingolipids are derived from lactose ceramides, where the first step is the acylation and desaturation of D-erythro-dihydrosphingosine. The ceramide is extracellularly glycosylated by glucosylation, followed by β-galactosylation to form lactose ceramide. Further extension can occur by glycosyltransferases and sulfotransferases.

We offer synthesizable sphingolipid molecules including:

• Neutral sphingolipids (glycolipids found primarily in the brain and peripheral nerve tissue)
• Acidic sphingolipids (supplied by sulfate groups in N-acetylneuraminic acid (NANA) or thioglycosides and located primarily in nerve endings)
• Basic sphingolipids
• Amphipathic sphingolipids
• Synthesis of glycerolipids

Glycerolipids (monogalactoside diesteroylglycerol (MGD) and digalactoside diesteroylglycerol (DGD)) are synthesized in the vesicle membranes of plastids. However, only a portion of their precursors originate from plastids. Biosynthesis of galactolipids requires coordinated transport of lipids between plastids and other organelles in vivo.

Transfer of the galactosyl group from UDP-Gal to diacylglycerol to produce MGD by galactosyltransferase.

Galactosyltransferase (GGGT) with galactolipid-dependent and cis-galactosyltransferase catalyzes the transfer of one galactose molecule from MGD to a second MGD molecule to obtain DGD.

We offer synthesizable glycerolipid molecules including:

• Neutral glycerolipids (typically containing one or two sugars linked to glycerol or diacylglycerol)
• Glycosphingolipids (glycerolipids containing at least one phosphate group attached to a sugar or glycerol)
• Sulfoglycoglycerolipids (contain sulfur atoms and are thought to be localized to acidic membranes)

Analysis of Glycolipids

The analysis of glycolipids usually involves the analysis of their structure, composition and properties. Depending on the purpose, a variety of methods are utilized, such as gas chromatography, liquid chromatography, mass spectrometry, and nuclear magnetic resonance, etc. BOC Sciences offers a wide range of glycolipid analyses to determine the purity of the glycolipids, characterize their structure, etc., and thus provide high quality glycolipids to our customers.

BOC Sciences offers a wide range of solutions for custom synthesis of lipids and provides a full range of analytical services. If you are interested in our services, please feel free to contact us.