2'-Fucosyllactose

2′-Fucosyllactose 2'-Fucosyllactose.svg 250px α-L-Fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-D-glucose (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 2′-FL 41263-94-9 147155 149055 correct FDA XO2533XO8R G00268 170484 C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O 1S/C18H32O15/c1-5-9(24)12(27)14(29)17(30-5)33-16-13(28)11(26)8(4-21)31-18(16)32-15(7(23)3-20)10(25)6(22)2-19/h2,5-18,20-29H,3-4H2,1H3/t5-,6-,7+,8+,9+,10+,11-,12+,13-,14-,15+,16+,17-,18-/m0/s1 HWHQUWQCBPAQQH-BWRPKUOHSA-N 1.681 g/cm3 18 32 15 11.9 240.0 g/L (in water) 2′-Fucosyllactose (2′-FL) is a 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.Vandenplas Yvan Berger Bernard Carnielli Virgilio Paolo Ksiazyk Janusz Lagström Hanna Sanchez Luna Manuel Migacheva Natalia Mosselmans Jean-Marc Picaud Jean-Charles Possner Mike Singhal Atul Wabitsch Martin 2018-08-24 Human Milk Oligosaccharides: 2′-Fucosyllactose (2′-FL) and Lacto-N-Neotetraose (LNnT) in Infant Formula Nutrients 10 9 1161 10.3390/nu10091161 2072-6643 6164445 30149573 free It was first discovered in the 1950s in human milk. The oligosaccharide's primary isolation technique has been in use since 1972.Showing metabocard for 2-Fucosyllactose (HMDB02098) http://www.hmdb.ca/metabolites/HMDB02098 Human Metabolome Database 19 October 2012 Structure 2′-FL consists of an L-fucose monomer in the α stereochemical configuration linked at the first carbon to a monomer of D-galactose in the β stereochemical configuration at the second carbon, which is in turn linked at the first carbon to a monomer of D-glucose (which may be in either the α or β configuration) at the fourth carbon. Production The compound may be biosynthesized in quantity using E. coli.U of I microbial engineer synthesizes 2-fucosyllactose to protect babies from pathogens http://www.news-medical.net/news/20120911/U-of-I-microbial-engineer-synthesizes-2-fucosyllactose-to-protect-babies-from-pathogens.aspx 19 October 2012 News MedicalChin Young-Wook Kim Ji-Yeong Lee Won-Heong Seo Jin-Ho Enhanced production of 2′-fucosyllactose in engineered Escherichia coli BL21star (DE3) by modulation of lactose metabolism and fucosyltransferase Journal of Biotechnology 2015 10.1016/j.jbiotec.2015.06.431 210 107–115 26193630Chin Young-Wook Seo Nari Kim Jae-Han Seo Jin-Ho Metabolic engineering of Escherichia coli to produce 2'-fucosyllactose via Salvage pathway of guanosine 5'-diphosphate (GDP)-L-fucose Biotechnology and Bioengineering 2016 10.1002/bit.26015 113 11 2443–2452 27217241 45579939 Chin Young-Wook Kim Ji-Yeong Kim Jae-Han Jung Sang-min Seo Jin-Ho Improved production of 2'-fucosyllactose in engineered Escherichia coli by expressing putative α-1,2-fucosyltransferase, WcfB from Bacteroides fragilis Journal of Biotechnology 2016 257 192–198 10.1016/j.jbiotec.2016.11.033 27919692 Metabolism thumb|left|alt=2FL.|The metabolic pathway for GDP--fucose and 2′-fucosyllactose (2-FL) biosynthesis in recombinant E. coli. November 2012 Human systemic metabolism of intact 2'-FL is limited. Like other HMOs, it is resistant to human digestive enzymes in the upper gut, meaning it reaches the colon relatively intact.MIAdmin 2018-01-29 Science Review: 2’Fucosyllactose Metagenics Institute https://www.metagenicsinstitute.com/ce-education/science-sheets/science-review-2fucosyllactose/ 2025-12-22 en-US The key site of 2'-FL metabolism is the intestinal microbiome. First, fucose is cleaved by α-fucosidases produced by gut bacteria such as Bifidobacterium spp. and Akkermansia spp..Zabel Bryan Yde Christian Clement Roos Paige Marcussen Jørn Jensen Henrik Max Salli Krista Hirvonen Johanna Ouwehand Arthur C. Morovic Wesley 2019-05-28 Novel Genes and Metabolite Trends in Bifidobacterium longum subsp. infantis Bi-26 Metabolism of Human Milk Oligosaccharide 2′-fucosyllactose https://www.nature.com/articles/s41598-019-43780-9 Scientific Reports en 9 1 7983 10.1038/s41598-019-43780-9 free 2045-2322 6538704 Padilla Loren Fricker Ashwana D. Luna Estefani Choudhury Biswa Hughes Elizabeth R. Panzetta Maria E. Valdivia Raphael H. Flores Gilberto E. 2024-02-22 Mechanism of 2'-fucosyllactose degradation by human-associated Akkermansia https://pubmed.ncbi.nlm.nih.gov/38299857 Journal of Bacteriology 206 2 e0033423 10.1128/jb.00334-23 1098-5530 10886448 38299857 The remaining lactose moiety is processed by β-galactosidases and other glycosidases. Further microbial fermentation results in short-chain fatty acids, such as acetate, as well as lactate, 1,2-propanediol, and butyrate.left Uses As with many other oligosaccharides, a characteristic of 2′-FL is its ability to protect against infectious diseasesTaylor Diane E. Rasko David A. Sherburne Richard Ho Clinton Jewel Laurence D. Lack of correlation between Lewis antigen expression by Helicobacter pylori and gastric epithelial cells in infected patients Gastroenterology 1998 1113–1122 10.1016/S0016-5085(98)70082-4 115 5 9797366 by preventing epithelial-level adhesion of toxins and pathogens.Lee Won-Heong Pathanibul Panchalee Quarterman Josh Jo Jung-Hyun Han Nam-Soo Miller Michael J Jin Yong-Su Seo Jin-Ho Whole cell biosynthesis of a functional oligosaccharide, 2'-fucosyllactose, using engineered Escherichia coli Microbial Cell Factories 2012 10.1186/1475-2859-11-48 11 48 22545760 3442965 free 2′-FL stimulates the growth of certain bifidobacteria and upregulation of receptorsAugust 2024 which collectively lend to toxic and pathogenic protection;August 2024 this is most prevalent in infants. Among the pathogens that 2′-FL is known to protect against are Campylobacter jejuni, Salmonella enterica (serotype Typhimurium), and Helicobacter pylori. References Category:Oligosaccharides