Monosaccharides, Oligosaccharides, Glycans and Polysaccharides

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About Monosaccharides, Oligosaccharides, Glycans and Polysaccharides

Sussex Research Laboratories Inc. prides itself on its ability to synthesize, purify and fully characterize complex carbohydrate systems such as oligosaccharides. From cancer antigens to glycosaminoglycan (GAG) oligosaccharides, we are experienced in virtually all aspects of oligosaccharide synthesis. The company has an excellent infrastructure including in-house high field NMR and mass spectrometry facilities for structural validation. We use chemical, enzymatic and chemoenzymatic approaches to synthesize our oligosaccharides that are purified and subject to full structural characterization via Proton, Carbon and 2-dimensional NMR techniques along with mass spectrometry.

Some Definitions

Carbohydrate is a generic term used interchangeably with terms such as saccharide, sugar, or glycan and includes other terms such monosaccharides, oligosaccharides and polysaccharides.

Monosaccharides are the basic carbohydrate building blocks of larger sugars (oligosaccharides, glycans, polysaccharides). Common monosaccharides found in eukaryotes are: N-Acetylgalactosamine (GalNAc), N-acetylglucosamine (GlcNAc), fucose (Fuc), galactose (Gal), glucose (Glc), mannose (Man), N-acetylneuraminic acid (sialic acid, NeuAc), xylose (Xyl), glucuronic acid (GlcA), and iduronic acid (IdUA).

Oligosaccharides are short chains or oligomers of monosaccharides (typically 2-10) connected via glycosidic linkages. Oligosaccharides may be referred to as glycans when conjugated to cell surface lipids or proteins. Oligosaccharides coat the majority of cell surface and circulatory proteins via conjugation to serine, threonine or asparagine. When conjugated to cell surface lipids and proteins, oligosaccharides are involved in a host of processes including but not limited to cellular recognition, cell adhesion, fertilization and immune function – little wonder that oligosaccharides are now being applied to diagnostic, therapeutic and vaccine development.

Glycans  refer to the  carbohydrate (oligosaccharide or polysaccharide) portion of  glycoconjugate, such as a glycoprotein, glycolipid, or a proteoglycan.

Glycosaminoglycans (GAGs) are a family of charged, highly sulfated oligosaccharides predominantly found as long unbranched polysaccharides containing repeating disaccharide units consisting either of N-acetylgalactosamine (GalNAc) or N-acetylglucosamine (GlcNAc) and uronic acids such as glucuronic acid (GlcA) or iduronic acid (IdoA).

Proteoglycans When GAGs are conjugated to proteins, the overall structure is referred to as a proteoglycan. These highly negatively charged glycans have been implicated in numerous biological processes including brain development, anticoagulation, cancer, inflammation, and spinal cord injury. Heparin, a pharmaceutical injectable, is widely used as an anticoagulant and is derived from mucosal tissues of porcine and bovine.

Polysaccharides (PS) are very long polymeric chains of monosaccharides connected via glycosidic linkages. While oligosaccharides generally contain 2-10 monosaccharide units, polysaccharides contain >10 and often >>1,000. Polysaccharides are found in plants and other lifeforms including bacteria and humans and may be neutral or charged. Some Glycosaminoglycans may be considered polysaccharides.

Lipopolysaccharides (LPS) consist of a polysaccharide conjugated to a lipid and are major components of the outer membrane of Gram-negative bacteria. LPS act as endotoxins eliciting strong immune responses in humans and are important in the development of vaccines. Our inventory of isolated LPS (and also capsular polysaccharides (CPS)) are derived from bacterial pathogens, including strains of Bordetella, E. coli, Francisella, Pseudomonas, Salmonella and Streptococcus to name just a few. LPS have been characterized via a variety of techniques including high field nmr and mass spectrometry. Associated antibodies may also be available in some cases.

{-4)-α-D-GalpNAcAN-(1-4)-α-D-GalpNAcAN-(1-3)-β-D-QuipNAc-(1-2)-β-D-QuipNAcFm-(1-}

Repeat unit of Francisella tularensis

Browse our offering below. We entertain custom syntheses of any carbohydrate.

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