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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
Structure of .ALPHA.-L-FUCOPYRANOSE

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

HIDE SMILES / InChI
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

Curator's Comment: referenced study was conducted in rat

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P53794
Gene ID: NA
Gene Symbol: SLC5A3
Target Organism: Homo sapiens (Human)
3.0 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A SV-40 immortalized murine endothelial cell line from peripheral lymph node high endothelium expresses a new alpha-L-fucose binding protein.
1993
L-fucose is accumulated via a specific transport system in eukaryotic cells.
1994 Sep 9
Structure and mechanism of L-fucose isomerase from Escherichia coli.
1997 Oct 17
Enhancement of glutamate release by L-fucose changes effects of glutamate receptor antagonists on long-term potentiation in the rat hippocampus.
2000 Jul-Aug
Fucose: biosynthesis and biological function in mammals.
2003 Jul
Inflammation, oxidative stress and L-fucose as indispensable participants in schistosomiasis-associated colonic dysplasia.
2014
Patents

Sample Use Guides

In Vivo Use Guide
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
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.
Name Type Language
.ALPHA.-L-FUCOPYRANOSE
Common Name English
FUCOPYRANOSE, .ALPHA.-L-
Common Name English
.ALPHA.-L-GALACTOPYRANOSE, 6-DEOXY-
Systematic Name English
L-FUCOSE .ALPHA.-FORM [MI]
Common Name English
.ALPHA.-L-FUCOSE
Common Name English
Code System Code Type Description
CAS
6696-41-9
Created by admin on Sat Dec 16 07:56:11 GMT 2023 , Edited by admin on Sat Dec 16 07:56:11 GMT 2023
PRIMARY
DRUG BANK
DB04473
Created by admin on Sat Dec 16 07:56:11 GMT 2023 , Edited by admin on Sat Dec 16 07:56:11 GMT 2023
PRIMARY
FDA UNII
OF086I9H7W
Created by admin on Sat Dec 16 07:56:11 GMT 2023 , Edited by admin on Sat Dec 16 07:56:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID901318356
Created by admin on Sat Dec 16 07:56:11 GMT 2023 , Edited by admin on Sat Dec 16 07:56:11 GMT 2023
PRIMARY
PUBCHEM
439554
Created by admin on Sat Dec 16 07:56:11 GMT 2023 , Edited by admin on Sat Dec 16 07:56:11 GMT 2023
PRIMARY
MERCK INDEX
m5578
Created by admin on Sat Dec 16 07:56:11 GMT 2023 , Edited by admin on Sat Dec 16 07:56:11 GMT 2023
PRIMARY Merck Index