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Product name: 3-Fucosyllactose
Synonym name: 3-O-α-LFucopyranosyllactose;3-O-α-L-Fucosyllactose；3FL
Catalogue No.: BP5161
Cas No.: 41312-47-4
Formula: C18H32O15
Mol Weight: 488.439
Botanical Source:
Type of Compound:
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HNMR of 3-Fucosyllactose
HPLC of 3-Fucosyllactose
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
256.2900
-2.9851
-2.9857
187.2399
.3587
.1054
Low
13.7570
5.1217
Yes
No
No
No
No
No
0.0
Yes
Yes
Yes
Yes
3-Fucosyllactose (3-Fucosyllactose, abbreviated as 3-FL), one of the most abundant oligosaccharides in human breast milk, has attracted widespread attention in the field of natural product pharmacology in recent years. As a functional oligosaccharide, 3-FL not only plays a key role in regulating the neonatal intestinal microecology but also demonstrates significant potential for immunomodulation, antibacterial effects, and promoting brain neurodevelopment. With the ongoing deepening of research into the structure and function of human milk oligosaccharides, the biological activity and molecular mechanisms of 3-FL have become increasingly elucidated, providing both theoretical and practical basis for its application in infant nutritional supplementation, immune disease intervention, and neurodevelopmental disorder treatment.
This paper aims to systematically review the chemical structure and physicochemical properties, sources and extraction techniques, pharmacological activity and mechanism of action of 3-fucosyllactose, druggability evaluation and pharmacokinetic characteristics, and to explore its clinical application prospects and future research directions, providing references for researchers and clinical practitioners in related fields.
3-Fucosyl lactose (3-Fucosyl-D-lactose) is a trisaccharide molecule formed by the connection of lactose (Galβ1-4Glc) and fucose (Fuc) through α1-3 glycosidic bonds. Its molecular formula is C20H36O15, and its molecular weight is 488.4390 Da. The structural feature of 3-FL lies in the specific way fucoidan residues are attached, giving it unique biological activity.
In terms of physicochemical properties, 3-FL exhibits high polarity, with a LogP value of -2.9851, indicating strong hydrophilicity. The extremely high topological pole surface area (TPSA) is 256.29 Ų, further indicating its good water solubility (solubility about 187.24 mg/mL). Due to its large polarity and molecular weight, 3-FL has relatively low permeability to the blood-brain barrier, suggesting that its direct action in the central nervous system is limited. Additionally, 3-FL did not show hERG channel inhibition, and Ames-induced mutagenic test results were zero, indicating high safety and promising drug potential.
3-Fucosyllactose is mainly found in human breast milk, with higher levels in the early stages of breastfeeding. Although its natural source is mainly breast milk, in recent years, as understanding of the oligosaccharides function of human breast milk has deepened, industrial production of 3-FL has gradually been realized, mainly through two pathways: microbial fermentation and enzyme-catalyzed synthesis.
Natural extracts
Traditionally, 3-FL extraction from breast milk is complex, requiring multiple steps such as whey separation, ultrafiltration, ion exchange, and chromatographic purification, with limited output and high costs, making it difficult to meet industrial demands.
Microbial fermentation method
Genetic engineering techniques are used to modify E. coli, yeast, or other probiotics to express specific fucoid-transferases (such as FUT9), catalyzing the synthesis of 3-FL in the presence of lactose. This method offers advantages such as low cost, high output, and stable processes, and has become the mainstream technology for 3-FL industrial production.
Enzyme-catalyzed synthesis
Purified fucoidyl transferase is performed by in vitro catalytic reaction, transferring fucose onto lactose molecules to synthesize 3-FL. This method operates under mild reaction conditions and produces high product purity, but the high cost of enzyme preparation limits its large-scale application.
In summary, microbial fermentation-based synthesis technology provides a feasible path for large-scale production of 3-FL, promoting its application in food, pharmaceuticals, and other fields.
3-Fucosyllactose, as a functional oligosaccharide, has multiple pharmacological activities, mainly including prebiotic effects, immune regulation, promotion of cranial neural development, and antibacterial effects.
3-FL can selectively promote the growth of gut probiotics (such as bifidobacteria and lactic acid bacteria), improving the balance of the intestinal microecosystem. Research shows that 3-FL, as a prebiotic, provides a specific carbon source, promotes the colonization of beneficial bacteria, inhibits pathogen growth, thereby maintaining intestinal barrier function and preventing intestinal infections and inflammation.
3-FL regulates the intestinal immune environment and enhances the body's immune defense capabilities. Its mechanisms include promoting the activation of immune cells (such as macrophages and dendritic cells), regulating cytokine secretion (such as IL-10, TNF-α), and participating in immune signal transduction by binding to immune-related receptors, reducing excessive inflammatory responses, and maintaining immune homeostasis.
3-FL plays an important role in neonatal brain development, especially promoting neuronal differentiation and synapse formation. Related studies indicate that 3-FL regulates glycosylase activity in the brain and the expression of glycoproteins on nerve cell surfaces, influences neural network construction, and promotes cognitive function and neural development.
3-FL can mimic the receptor structure of pathogens, competitively binding to block the pathogen's adhesion to intestinal epithelial cells, thereby exerting anti-infective effects. It is especially effective against common intestinal pathogens such as Helicobacter pylori and E. coli, reducing the risk of infection.
The biological function of 3-FL is closely related to the molecular targets of its specific actions. Current research focuses on its targets and signaling pathways in the field of brain neurodevelopment.
ST8SIA2: Encodes polysialicyltransferase, participating in the synthesis of polysialic acid on the surface of nerve cells, affecting neuronal migration and axon orientation. 3-FL promotes neuronal development and synaptic plasticity by regulating ST8SIA2 expression.
B3GNT5: β-1,3-N-acetylglucosyltransferase, involved in glycan synthesis, affects intercellular signaling and cell adhesion. 3-FL may regulate the glycosylation state on the surface of neurons by regulating B3GNT5 activity, thereby promoting neural network formation.
FUT9: Fucoidase catalyzes the transfer of fucose residues, affecting the glycan structure on the surface of nerve cells. 3-FL, as a product of FUT9, regulates the enzyme's activity in feedback and maintains glycosylation balance during neurodevelopment.
CD24: Cell surface glycoprotein involved in immune regulation and neurodevelopment. 3-FL regulates immune cell function and neuronal signal transduction by interacting with CD24.
NCAM1: Neuronal adhesion molecule 1, a key neurodevelopmental regulatory factor. 3-FL promotes neuronal adhesion and synapse formation by affecting the glycosylation modification of NCAM1.
3-FL regulates the expression and glycosylation state of these targets, influences neuronal differentiation, migration, and synaptic formation, and promotes brain nerve development. At the same time, in gut immune regulation and antibacterial effects, it mimics the receptor structure of pathogens, blocks pathogen adhesion, regulates immune cell activity, and maintains intestinal barrier function.
Druggability evaluation of 3-FL indicates good safety and pharmacological activity potential.
In summary, 3-FL is suitable for use in gut-related diseases and as a nutritional supplement for infants and young children. It has good druggability, but further optimization of the administration route is needed for central nervous system diseases.
With further in-depth research into the biological functions of 3-FL, its clinical application prospects are broad, mainly reflected in the following aspects:
Nutritional supplements for infants and young children
As a representative oligosaccharide of human milk, 3-FL has been widely added to formula milk powder, aiming to mimic the prebiotic and immunomodulatory functions of breast milk, promoting gut health and immune system development in infants and young children.
Adjunctive therapy for immune diseases
Based on its immunomodulatory effects, 3-FL is expected to be used to prevent and adjuvant the treatment of enteritis, allergic diseases, and immunodeficiency-related conditions, improving patients' immune status.
Neurodevelopmental disorder intervention
The neurodevelopmental effect of 3-FL offers potential therapeutic strategies for neurodevelopmental disorders such as autism spectrum disorder and attention deficit hyperactivity disorder, and in the future, targeted therapy can be combined with delivery techniques.
Development of anti-infective drugs
Its antimicrobial mechanism provides ideas for developing novel anti-infective drugs, especially in the context of increasingly severe antibiotic resistance, where 3-FL and its derivatives may become important candidates for alternative therapies.
Future research should focus on the pharmacokinetic characteristics, formulation development, and clinical efficacy evaluation of 3-FL, promoting its transition from functional foods to drug development.
3-fucosyllactose, as an important component of natural human milk oligosaccharides, demonstrates broad application potential in prebiotics, immune regulation, brain development, and antibacterial fields due to its unique chemical structure and diverse biological activities. Its excellent safety and druggability lay the foundation for clinical translation. In the future, with advances in synthetic technology and deeper elucidation of its mechanisms, 3-FL is expected to play a greater role in infant nutrition, immune disease treatment, and neurodevelopmental disorder intervention, becoming an important research hotspot and new clinical application star in the field of natural product pharmacology.
Shenshuai
Wenjing
Hedandan
