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-PHYPRBDBSA-N
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m1/s1
| Molecular Formula | C6H12O5 |
| Molecular Weight | 164.1565 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
α-D-Fucopyranose (aka α-D-fucose) is a six-carbon deoxy monosaccharide. It is equivalent to 6-deoxy-D-galactose. It acts as a non-metabolizable analog of L-arabinose and inhibits induction of the L-arabinose operon in some bacteria. Other bacteria possess a mutant araC gene where D-fucose acts as a gratuitous inducer of the L-arabinose operon. D-fucose also acts as an activator of the galS promotor in E. coli. Because of its ability to regulate gene expression, there has been some interest in exploring D-fucose as a lead compound in neurodegenerative diseases or cancer.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P0A9E0 Gene ID: 944780.0 Gene Symbol: araC Target Organism: Escherichia coli (strain K12) |
|||
Target ID: P25748 Gene ID: 949043.0 Gene Symbol: galS Target Organism: Escherichia coli (strain K12) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fucose: biosynthesis and biological function in mammals. | 2003-07 |
|
| Control of transcription of gal repressor and isorepressor genes in Escherichia coli. | 1993-01 |
|
| Induction of beta-galactosidase in Lactobacillus plantarum. | 1974-10 |
|
| D-Fucose as a gratuitous inducer of the L-arabinose operon in strains of Escherichia coli B-r mutant in gene araC. | 1971-07 |
Patents
Sample Use Guides
0.4 mM and 1 mM of D-fucose was added to E. coli cultures in a media of 1 % tryptone, 0.5% yeast extract, 0.5% NaCl, and 0.1% glucose. Inhibition of operon induction was measured as the rate of isomerase production. In the strain UP1006(ara+) the degree of inhibition by D-fucose increased with an increase in D-fucose concentration and D-fucose appears to be acting as a competitive inhibitor. In 15 out of 18 D-fucose resistant mutants L-arabinose isomerase specific activity is 1.2 to 150 fold higher than their constitutive level, clearly indicating that L-arabinose is now acting as an inducer.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:46:34 GMT 2025
by
admin
on
Mon Mar 31 21:46:34 GMT 2025
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| Record UNII |
K15K52FOK4
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| Record Status |
Validated (UNII)
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| Record Version |
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444200
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DTXSID301318477
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6189-71-5
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DB03485
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K15K52FOK4
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