Chemistry:2'-Fucosyllactose
Names | |
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IUPAC name
α-L-Fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-D-glucose
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Systematic IUPAC name
(2R,3R,4R,5R)-4-{[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,3,5,6-tetrahydroxyhexanal | |
Other names
2′-FL
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
KEGG | |
PubChem CID
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UNII | |
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Properties | |
C18H32O15 | |
Molar mass | 488.439 g·mol−1 |
Density | 1.681 g/cm3 |
240.0 g/L (in water) | |
Acidity (pKa) | 11.9 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
2′-Fucosyllactose (2′-FL) is an oligosaccharide, more precisely, fucosylated, neutral trisaccharide composed of L-fucose, D-galactose, and D-glucose units. It is the most prevalent human milk oligosaccharide (HMO) naturally present in human breast milk, making up about 30% of all of HMOs.[1] It was first discovered in the 1950s in human milk. The oligosaccharide's primary isolation technique has been in use since 1972.[2]
Production
This compound may be biosynthesized in quantity using E. coli.[3][4][5][6]
Metabolism
File:2′-fucosyllactose Reaction Diagram.tiff
Uses
As with other oligosaccharides, a widely regarded characteristic of 2'-fucosyllactose is its ability to protect against infectious diseases[7] namely in preventing epithelial level adhesions of toxins and pathogens.[8] The 2FL stimulates the growth of certain bifidobacteria and receptor analogons which lends to toxic and pathogenic protection, all this being most prevalent in infants. Among the pathogens that 2FL is known to protect against are Campylobacter jejuni, Salmonella enterica serotype Typhimurium, Helicobacter pylori, among others.[8]
References
- ↑ Vandenplas, Yvan; Berger, Bernard; Carnielli, Virgilio Paolo; Ksiazyk, Janusz; Lagström, Hanna; Sanchez Luna, Manuel; Migacheva, Natalia; Mosselmans, Jean-Marc et al. (2018-08-24). "Human Milk Oligosaccharides: 2′-Fucosyllactose (2′-FL) and Lacto-N-Neotetraose (LNnT) in Infant Formula". Nutrients 10 (9): 1161. doi:10.3390/nu10091161. ISSN 2072-6643. PMID 30149573.
- ↑ "Showing metabocard for 2-Fucosyllactose (HMDB02098)". Human Metabolome Database. http://www.hmdb.ca/metabolites/HMDB02098. Retrieved 19 October 2012.
- ↑ "U of I microbial engineer synthesizes 2-fucosyllactose to protect babies from pathogens". News Medical. http://www.news-medical.net/news/20120911/U-of-I-microbial-engineer-synthesizes-2-fucosyllactose-to-protect-babies-from-pathogens.aspx. Retrieved 19 October 2012.
- ↑ Chin, Young-Wook; Kim, Ji-Yeong; Lee, Won-Heong; Seo, Jin-Ho (2015). "Enhanced production of 2′-fucosyllactose in engineered Escherichia coli BL21star (DE3) by modulation of lactose metabolism and fucosyltransferase". Journal of Biotechnology 210: 107–115. doi:10.1016/j.jbiotec.2015.06.431. PMID 26193630.
- ↑ Chin, Young-Wook; Seo, Nari; Kim, Jae-Han; Seo, Jin-Ho (2016). "Metabolic engineering of Escherichia coli to produce 2'-fucosyllactose via Salvage pathway of guanosine 5'-diphosphate (GDP)-L-fucose". Biotechnology and Bioengineering 113 (11): 2443–2452. doi:10.1002/bit.26015. PMID 27217241.
- ↑ Chin, Young-Wook; Kim, Ji-Yeong; Kim, Jae-Han; Jung, Sang-min; Seo, Jin-Ho (2016). "Improved production of 2'-fucosyllactose in engineered Escherichia coli by expressing putative α-1,2-fucosyltransferase, WcfB from Bacteroides fragilis". Journal of Biotechnology 257: 192–198. doi:10.1016/j.jbiotec.2016.11.033. PMID 27919692.
- ↑ Taylor, Diane E.; Rasko, David A.; Sherburne, Richard; Ho, Clinton; Jewel, Laurence D. (1998). "Lack of correlation between Lewis antigen expression by Helicobacter pylori and gastric epithelial cells in infected patients". Gastroenterology 115 (5): 1113–1122. doi:10.1016/S0016-5085(98)70082-4. PMID 9797366.
- ↑ 8.0 8.1 Lee, Won-Heong; Pathanibul, Panchalee; Quarterman, Josh; Jo, Jung-Hyun; Han, Nam-Soo; Miller, Michael J; Jin, Yong-Su; Seo, Jin-Ho (2012). "Whole cell biosynthesis of a functional oligosaccharide, 2'-fucosyllactose, using engineered Escherichia coli". Microbial Cell Factories 11: 48. doi:10.1186/1475-2859-11-48. PMID 22545760.
Original source: https://en.wikipedia.org/wiki/2'-Fucosyllactose.
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