An oligosaccharide (from the Greek ολίγος oligos, a few, and σάκχαρ sacchar, sugar) is a saccharide polymer containing a small number (typically three to nine[1][2][3][4]) of simple sugars (monosaccharides). Oligosaccharides can have many functions; for example, they are commonly found on the plasma membrane of animal cells where they can play a role in cell-to-cell recognition.
In general, they are found either O- or 'N-linked to compatible amino acid side-chains in proteins or to lipid moieties (see glycans). N-linked Oligosaccharides are found attached to asparagine via beta linkage to the amine nitrogen of the side chain.[5] Alternately, O-linked oligosaccharides are generally attached to threonine or serine on the OH group of the side chain.
Contents
- 1 Examples
- 2 Therapeutic effects
- 3 Role in human reproduction system
- 4 Role in mother-to-child transmission of HIV-1
- 5 Sources
- 6 See also
- 7 References
Examples
Fructo-oligosaccharides (FOS), which are found in many vegetables, consist of short chains of fructose molecules. (Inulin has a much higher degree of polymerization than FOS and is a polysaccharide.) Galactooligosaccharides (GOS), which also occur naturally, consist of short chains of galactose molecules. These compounds can be only partially digested by humans.
Oligosaccharides are often found as a component of glycoproteins or glycolipids and as such are often used as chemical markers, often for cell recognition. An example is ABO blood type specificity. A and B blood types have two different oligosaccharide glycolipids embedded in the cell membranes of the red blood cells, AB-type blood has both, while O blood type has neither.
Mannan oligosaccharides (MOS) are widely used in animal feed to improve gastrointestinal health, energy levels and performance. They are normally obtained from the yeast cell walls of Saccharomyces cerevisiae. Research at the University of Illinois has demonstrated that mannan oligosaccharides differ from other oligosaccharides in that they are not fermentable and their primary mode of actions include agglutination of type-1 fimbrae pathogens and immunomodulation[6]
Therapeutic effects
When oligosaccharides are consumed, the undigested portion serves as food for the intestinal microflora. Depending on the type of oligosaccharide, different bacterial groups are stimulated or suppressed.[7][8]
Clinical studies have shown that administering FOS, GOS, or inulin can increase the number of these beneficial bacteria in the colon while simultaneously reducing the population of harmful bacteria.[9]
Role in human reproduction system
The Sialyl-Lewisx Oligosaccharide identified in a 2011 study, seems to be the most abundant carbohydrate receptor present in the outer coating (zona pellucida (ZP)) of the human ova, and is implicated as a large factor of Sperm-ZP binding leading to fertilization. These Sialyl-Lewisx branches are much more common on the ovum than on any other kind of body cell; they completely coat it. The discovery of the largest receptor on the human ovum may help improve infertility research.[10][11]
Role in mother-to-child transmission of HIV-1
Breast-feeding is the highest prevalence factor of postnatal transmission of HIV-1. However, most breast-fed infants do not contract the virus from the infected mother despite the continuous exposure. The Lewis antigen glycans in human milk compete with HIV-1 glycoprotein-120 and binds to the dendritic cell-specific ICAM3-grabbing non-integrin (DC-SIGN) on human dendritic cells. The glycans inhibit the transfer of the virus to the CD4 T lymphocytes. Because the human milk oligosaccharides carry one more of the Lewis antigen glycan, it's hypothesized that they do compete with gp120 for binding.[12]
Sources
Oligosaccharides are one of the components of fibre, found in plants. FOS and inulin are found naturally in Jerusalem artichoke, burdock, chicory, leeks, onions, and asparagus. FOS products derived from chicory root contain significant quantities of inulin, a fiber widely distributed in fruits, vegetables and plants. Inulin is a significant part of the daily diet of most of the world’s population. FOS can also be synthesized by enzymes of the fungus Aspergillus niger acting on sucrose. GOS is naturally found in soybeans and can be synthesized from lactose (milk sugar). FOS, GOS, and inulin are available as nutritional supplements in capsules, tablets, and as a powder.
Not all natural oligosaccharides occur as components of glycoproteins or glycolipids. Some, such as the raffinose series, occur as storage or transport carbohydrates in plants. Others, such as maltodextrins or cellodextrins, result from the microbial breakdown of larger polysaccharides such as starch or cellulose.
See also
- Oligosaccharide synthesis
- Oligosaccharide nomenclature
- Polysaccharide
- Mannan Oligosaccharides, MOS
- Isomaltooligosaccharide, IMO
References
- ^ Oligosaccharides at the US National Library of Medicine Medical Subject Headings (MeSH)
- ^ Dairy Science and Technology, second edition. P. Walstra, J.T.M. Wouters and T.J. Geurts. CRC, Taylor & Francis, 2008
- ^ Understanding Nutrition, Eleventh Edition. E. Whitney, S. R. Rolfes. Thomson Wadsworth, 2008
- ^ http://www.britannica.com/EBchecked/topic/427621/oligosaccharide
- ^ Voet, Donald; Voet, Judith; Pratt, Charlotte (2013). Fundamentals of Biochemistry: Life at the Molecular Level (4th ed.). Hoboken, NJ: John Wiley & Sons, Inc. ISBN 978-0470-54784-7.
- ^ rishi (October 2003). "In vitro fermentation characteristics of selected oligosaccharides by swine fecal microflora" (Abstract (free)). 81 (10). pp. 2505–2514. Retrieved 30 March 2013.
- ^ Bode, L. (2009). "Human milk oligosaccharides: prebiotics and beyond.". Nutrition Reviews 67 (2): S183–91. doi:10.1111/j.1753-4887.2009.00239.x.
- ^ De Filippo, C., Cavalieri, D., Di Paola, M., Ramazzotti, M., Poullet, J. B., Massart, S.; et al. (2010). "Impact of diet in shaping gut microbiota revealed by a comparative study in children from Europe and rural Africa.". Proceedings of the National Academy of Sciences 107 (33): 14691–14696. doi:10.1073/pnas.1005963107. PMC 2930426. PMID 20679230.
- ^ Macfarlane GT, Steed H. and Macfarlane S. (2008). "Bacterial metabolism and health-related effects of galacto-oligosaccharides and other prebiotics". J. Appl. Microbiol. 104 (2): 305–344. doi:10.1111/j.1365-2672.2007.03520.x. PMID 18215222.
- ^ http://news.sciencemag.org/sciencenow/2011/08/the-sweet-meeting-of-sperm-and-e.html
- ^ http://www.sciencemag.org/content/333/6050/1761
- ^ Hong, Ninonuevo, Lee, Bode, Librill, "Human milk oligosaccharides reduce HIV-1-gp120 binding to dendritic cell-specific ICAM3-grabbing non-integrin (DC-SIGN)", "pubmed.gov."
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Types of carbohydrates
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| General |
- Aldose
- Ketose
- Furanose
- Pyranose
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| Geometry |
- Anomer
- Cyclohexane conformation
- Mutarotation
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| Monosaccharides |
| Dioses |
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| Trioses |
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| Tetroses |
|
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| Pentoses |
- Aldopentoses
- Arabinose
- Lyxose
- Ribose
- Xylose
- Ketopentoses
- Deoxy sugars
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| Hexoses |
- Aldohexoses
- Allose
- Altrose
- Galactose
- Glucose
- Gulose
- Idose
- Mannose
- Talose
- Ketohexoses
- Fructose
- Psicose
- Sorbose
- Tagatose
- Deoxy sugars
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| Heptoses |
- Ketoheptoses
- Mannoheptulose
- Sedoheptulose
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| Above 7 |
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| Multiple |
| Disaccharides |
- Cellobiose
- Isomaltose
- Lactose
- Lactulose
- Maltose
- Sucrose
- Trehalose
- Turanose
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| Trisaccharides |
- Maltotriose
- Melezitose
- Raffinose
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| Tetrasaccharides |
|
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Other
oligosaccharides |
- Acarbose
- Fructooligosaccharide (FOS)
- Galactooligosaccharide (GOS)
- Isomaltooligosaccharide (IMO)
- Maltodextrin
- Mannan-oligosaccharides (MOS)
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| Polysaccharides |
- Beta-glucan
- Lentinan
- Sizofiran
- Zymosan
- Cellulose
- Chitin
- Dextrin / Dextran
- Fructose / Fructan
- Galactose / Galactan
- Glucose / Glucan
- Levan beta 2→6
- Mannan
- Starch
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Index of biochemical families
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| Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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| Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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| Nucleic acids |
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| Proteins |
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| Other |
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