2'-Fucosyllactose

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.

Metabolism

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.

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.. 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.

Uses

As with many other oligosaccharides, a characteristic of 2′-FL is its ability to protect against infectious diseases by preventing epithelial-level adhesion of toxins and pathogens. 2′-FL stimulates the growth of certain bifidobacteria and upregulation of receptors which collectively lend to toxic and pathogenic protection; 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

References

1. (2018-08-24). "Human Milk Oligosaccharides: 2′-Fucosyllactose (2′-FL) and Lacto-N-Neotetraose (LNnT) in Infant Formula". Nutrients.
2. "Showing metabocard for 2-Fucosyllactose (HMDB02098)". Human Metabolome Database.
3. "U of I microbial engineer synthesizes 2-fucosyllactose to protect babies from pathogens". News Medical.
4. (2015). "Enhanced production of 2′-fucosyllactose in engineered ''Escherichia coli'' BL21star (DE3) by modulation of lactose metabolism and fucosyltransferase". Journal of Biotechnology.
5. (2016). "Metabolic engineering of ''Escherichia coli'' to produce 2'-fucosyllactose via Salvage pathway of guanosine 5'-diphosphate (GDP)-L-fucose". Biotechnology and Bioengineering.
6. (2016). "Improved production of 2'-fucosyllactose in engineered ''Escherichia coli'' by expressing putative α-1,2-fucosyltransferase, WcfB from ''Bacteroides fragilis''". Journal of Biotechnology.
7. MIAdmin. (2018-01-29). "Science Review: 2’Fucosyllactose {{!}} Metagenics Institute".
8. Zabel, Bryan. (2019-05-28). "Novel Genes and Metabolite Trends in Bifidobacterium longum subsp. infantis Bi-26 Metabolism of Human Milk Oligosaccharide 2′-fucosyllactose". Scientific Reports.
9. Padilla, Loren. (2024-02-22). "Mechanism of 2'-fucosyllactose degradation by human-associated Akkermansia". Journal of Bacteriology.
10. (1998). "Lack of correlation between Lewis antigen expression by Helicobacter pylori and gastric epithelial cells in infected patients". Gastroenterology.
11. (2012). "Whole cell biosynthesis of a functional oligosaccharide, 2'-fucosyllactose, using engineered Escherichia coli". Microbial Cell Factories.