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L-Fucose

Catalog Number
ACM2438804-2
CAS
2438-80-4
Structure
IUPAC Name
(2S,3R,4R,5S)-2,3,4,5-Tetrahydroxyhexanal
Synonyms
6-Deoxy-L-galactos
Molecular Weight
164.16
Molecular Formula
C6H12O5
Canonical SMILES
CC(C(C(C(C=O)O)O)O)O
InChI
InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4+,5+,6-/m0/s1
InChI Key
PNNNRSAQSRJVSB-KCDKBNATSA-N
Boiling Point
211.61 °C
Melting Point
150-153 °C(lit.)
Flash Point
149.7 °C
Purity
98%
Density
1.1738 g/cm³
Solubility
Soluble in water
Appearance
Powder
Storage
Inert atmosphere, store in freezer, under -20 °C
Active Content
95%
Physical State
Solid
Typical Applications
Use as emulsion stabilizer, dispersing agent.
Spec Sheet
Case Study

L-Fucose Enhances Fucosylation in Colorectal Cancer Cells by Promoting Serine Accumulation

L-Fucose Enhances Fucosylation in Colorectal Cancer Cells by Promoting Serine Accumulation Yao, Ye, et al. Food & Function 14.9 (2023): 4314-4326.

Fucosylation, a post-translational modification, plays a critical role in cellular processes and has been linked to various diseases, including colorectal cancer (CRC). L-Fucose, a key substrate for fucosylation, has been reported to have anticancer properties and can increase fucosylation. However, the relationship between its tumor-suppressive effects and its ability to modulate fucosylation remains unclear.
In this study, we demonstrate that L-fucose enhances fucosylation and inhibits cancer cell growth in colorectal cancer cells (HCT-116), but not in normal cells (HCoEpic). This effect may be attributed to the induction of pro-apoptotic fucosylated proteins in HCT-116 cells. RNA-sequencing analysis revealed that L-fucose supplementation led to the upregulation of genes involved in serine biosynthesis (e.g., PSAT1) and a decrease in genes related to serine consumption, a response unique to HCT-116 cells. Furthermore, elevated serine levels in HCT-116 cells, along with increased α1,3/6-fucosylation following exogenous serine supplementation, confirmed that L-fucose enhances fucosylation by promoting intracellular serine accumulation.
Knockdown of PSAT1 or serine deficiency reduced fucosylation, while PSAT1 knockdown also attenuated L-fucose's inhibitory effects on cell proliferation and migration. Interestingly, increased α1,3/6-fucosylation and upregulation of PSAT1 were also observed in colorectal tumor tissues from CRC patients. These findings reveal a novel role for serine synthesis and PSAT1 in regulating fucosylation and suggest the potential of L-fucose in CRC therapy.

L-Fucose as a Candidate Monosaccharide Neuromodulator for Alleviating Alzheimer's Synaptic Deficits

L-Fucose as a Candidate Monosaccharide Neuromodulator for Alleviating Alzheimer's Synaptic Deficits Lucente, J. D., et al. "L-Fucose is a candidate monosaccharide neuromodulator and mitigates Alzheimer's synaptic deficits." bioRxiv (2022): 2022-08.

In this study, we uncovered a novel signaling role for L-fucose, a structurally distinct monosaccharide. Our findings demonstrate that L-fucose enhances excitatory neurotransmission and long-term potentiation (LTP) at Schaffer-collateral-CA1 synapses. We observed that L-fucose was released by neurons in an activity- and store-dependent manner, leading to rapid signaling changes that increased presynaptic neurotransmitter release. These effects were shown to depend on L-fucose metabolism through the salvage pathway, mediated by fucokinase (FUK). Consequently, L-fucose may represent the first described monosaccharide neuromodulator acting via a metabolic-signaling mechanism.
L-Fucose Modulates Excitatory Neurotransmission
To assess the effects of L-fucose on synaptic function, we perfused hippocampal slices from 12-month-old wild-type (WT) and 5xFAD mice with 200 µM L-fucose and recorded field excitatory postsynaptic potentials (fEPSP) at Schaffer-collateral-CA1 synapses. In WT slices, fEPSP amplitudes increased within 1-2 minutes of perfusion, plateaued around 10 minutes, and returned to baseline within 5 minutes after the perfusion ceased. To confirm the specificity of L-fucose's effects, we tested three structurally similar monosaccharides: D-fucose (the enantiomer of L-fucose), D-galactose (which differs from D-fucose by a hydroxyl group at C-6), and D-mannose (which differs from D-galactose by the stereochemistry of the hydroxyl groups at C-2 and C-4). None of these monosaccharides altered fEPSP, suggesting that L-fucose specifically facilitates synaptic transmission.
In contrast, L-fucose did not induce fEPSP facilitation in 5xFAD slices, even after prolonged perfusion. However, increasing the concentration of L-fucose in these slices eventually triggered a delayed and less pronounced response, highlighting the potential of L-fucose to modulate synaptic activity, albeit with slower kinetics and a reduced effect in the Alzheimer's model.

Custom Q&A

What is the product name of CAS number 2438-80-4?

The product name is L-Fucose.

What are some synonyms for L-Fucose?

Some synonyms for L-Fucose are Fucose and L-Galactose, 6-deoxy-.

What is the molecular weight of L-Fucose?

The molecular weight of L-Fucose is 164.16.

What is the molecular formula of L-Fucose?

The molecular formula of L-Fucose is C6H12O5.

What is the active ingredient percentage of L-Fucose?

The active ingredient percentage of L-Fucose is 95%.

What is the physical state of L-Fucose?

The physical state of L-Fucose is solid.

What are some typical applications of L-Fucose?

Some typical applications of L-Fucose are as an emulsion stabilizer and dispersing agent.

In what form is L-Fucose commonly used?

L-Fucose is commonly used in its solid form.

What is the main function of L-Fucose as an emulsion stabilizer?

The main function of L-Fucose as an emulsion stabilizer is to help prevent the separation of the different components in an emulsion.

How does L-Fucose work as a dispersing agent?

L-Fucose works as a dispersing agent by helping to evenly distribute particles within a solution or mixture.

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