Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C6H12O5 |
Molecular Weight | 164.1565 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O
InChI
InChIKey=SHZGCJCMOBCMKK-SXUWKVJYSA-N
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m0/s1
L-fucose is a hexose deoxy sugar found on N-linked glycans on mammalian, insect and plant cell surfaces. Deficiency in L-fucose has been observed in several pathological conditions including cancer and atherosclerosis. On the other hand, L-fucose is an inhibitor of the sodium/myo-inositol transporter which may play a roll in the development of diabetes. L-fucose is has been considered as a diagnostic biomarker in several forms fo cancer.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7208543
Curator's Comment: referenced study was conducted in rat
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P53794 Gene ID: NA Gene Symbol: SLC5A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1313850 |
3.0 mM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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A SV-40 immortalized murine endothelial cell line from peripheral lymph node high endothelium expresses a new alpha-L-fucose binding protein. | 1993 |
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L-fucose is accumulated via a specific transport system in eukaryotic cells. | 1994 Sep 9 |
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Structure and mechanism of L-fucose isomerase from Escherichia coli. | 1997 Oct 17 |
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Enhancement of glutamate release by L-fucose changes effects of glutamate receptor antagonists on long-term potentiation in the rat hippocampus. | 2000 Jul-Aug |
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Fucose: biosynthesis and biological function in mammals. | 2003 Jul |
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Inflammation, oxidative stress and L-fucose as indispensable participants in schistosomiasis-associated colonic dysplasia. | 2014 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7208543
Curator's Comment: referenced study was conducted in rat
Rats were administered 100 mg/kg intraperitoneally or 75 micrograms intraventricularly prior to training in a shuttle box avoidance and in shock motivated brightness discrimination tasks. Both treatment groups significantly improved the retention of learned behavior 24 hours later. In naive animals, intraventricularly applied L-fucose (75-200 ug) caused an increase in the rate of protein synthesis in the hippocampus, significantly increasing the total proteins and mainly attributed to Tris-insoluble protein fractions.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5658445
12.5 mg/mL of L-fucose was added to several different cell line cultures in Wymouth's medium containing 10% calf serum, 50 units/mL penicillin, 50 ug/mL streptomycin, and 30 ug/mL kanamycin. L-fucose had marked effects on cell morphology in the following cell lines: 3T3, BHK21, and Human Skin Fibroblasts. The 3T3 mouse fibroblasts showed a marked inhibition of growth when cultured with L-fucose, as well as the decreased incorporation of uridine, leucine, and thymidine in growing but not confluent cultures.
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m5578
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PRIMARY | Merck Index |
SUBSTANCE RECORD