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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:40:10 UTC

HMDB ID

HMDB0000174

Secondary Accession Numbers

HMDB00174
HMDB0059624
HMDB59624

Metabolite Identification

Common Name

L-Fucose

Description

Fucose (CAS: 2438-80-4) is a hexose deoxy sugar with the chemical formula C6H12O5. L-Fucose (6-deoxy-L-galactose) is a monosaccharide that is a common component of many N- and O-linked glycans and glycolipids produced by mammalian cells. It is the fundamental subunit of the fucoidan polysaccharide. As a free sugar, L-fucose is normally found at very low levels in mammals. It is unique in that it is the only levorotatory sugar synthesized and utilized by mammals. Fucose polymers are synthesized by fucosyltransferases. All fucosyltransferases utilize a nucleotide-activated form of fucose, GDP-fucose, as a fucose donor in the construction of fucosylated oligosaccharides. The ABO blood group antigens are among the most well known fucosylated glycans. The alpha-1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. Fucose is metabolized by an enzyme called alpha-fucosidase. Fucose is secreted in urine when the liver is damaged. Free L-fucose in serum and urine can be used as a marker for cancer, cirrhosis, alcoholic liver disease and gastric ulcers (PMID: 2311216 , 8488966 ). Elevated levels of serum fucose have been reported in breast cancer, ovarian cancer, lung cancer, liver cancer, diabetes, and cardiovascular disease. It has been shown that feeding rats a diet high in L-fucose induces neuropathy similar to that seen in diabetics.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-L-Fuc	ChEBI
alpha-L-Fucp	ChEBI
a-L-Fuc	Generator
α-L-Fuc	Generator
a-L-Fucose	Generator
α-L-fucose	Generator
a-L-Fucp	Generator
α-L-fucp	Generator
6-Deoxy-L-galactopyranose	HMDB
6-Deoxy-L-galactose	HMDB
6-Deoxy-alpha-L-galactopyranose	HMDB
6-Deoxy-alpha-L-galactose	HMDB
6-Deoxy-α-L-galactopyranose	HMDB
6-Deoxy-α-L-galactose	HMDB
alpha-L-Fucopyranose	HMDB
alpha-L-Fucose	HMDB
α-L-Fucopyranose	HMDB
α-L-Fucose	HMDB
(-)-Fucose	HMDB
6-Desoxygalactose	HMDB
Fucose	HMDB
L-(-)-Fucose	HMDB
L-Fucose	HMDB
L-Galactomethylose	HMDB

Chemical Formula

C₆H₁₂O₅

Average Molecular Weight

164.1565

Monoisotopic Molecular Weight

164.068473494

IUPAC Name

(2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol

Traditional Name

α-L-fucose

CAS Registry Number

6696-41-9

SMILES

C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O

InChI Identifier

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

InChI Key

SHZGCJCMOBCMKK-SXUWKVJYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-fucopyranose (CHEBI:42548 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Cell

Fibroblasts (HMDB: HMDB0000174)
Neuron (HMDB: HMDB0000174)

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0000174)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 22411374)

Cellular substructure

Cytoplasm (HMDB: HMDB0000174)
Extracellular (HMDB: HMDB0000174)

Organelle

Lysosome (HMDB: HMDB0000174)

Source

Exogenous

Exogenous (HMDB: HMDB0000174)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Pulse

Bean

Mung bean (FooDB: FOOD00200)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Spice

Caraway (FooDB: FOOD00043)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Milk and milk products (FooDB: FOOD00863)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Endogenous

Endogenous (HMDB: HMDB0000174)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fructose and Mannose Degradation (PathBank: SMP0087296)

Disease pathway

Fructose Intolerance, Hereditary (PathBank: SMP0120657)
Fructosuria (PathBank: SMP0120625)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	985 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	827 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-1.9	ChemAxon
logS	0.7	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.38 m³·mol⁻¹	ChemAxon
Polarizability	15.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	139.981	30932474
DeepCCS	[M-H]-	137.659	30932474
DeepCCS	[M-2H]-	172.377	30932474
DeepCCS	[M+Na]+	146.618	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	133.6	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	129.5	32859911
AllCCS	[M+Na-2H]-	130.8	32859911
AllCCS	[M+HCOO]-	132.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	0.79 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7099 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	245.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Fucose	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O	3109.0	Standard polar	33892256
L-Fucose	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O	1503.5	Standard non polar	33892256
L-Fucose	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O	1434.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Fucose,1TMS,isomer #1	C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O	1458.1	Semi standard non polar	33892256
L-Fucose,1TMS,isomer #2	C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O	1468.2	Semi standard non polar	33892256
L-Fucose,1TMS,isomer #3	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O	1481.0	Semi standard non polar	33892256
L-Fucose,1TMS,isomer #4	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C	1496.0	Semi standard non polar	33892256
L-Fucose,2TMS,isomer #1	C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O	1495.4	Semi standard non polar	33892256
L-Fucose,2TMS,isomer #2	C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O	1529.5	Semi standard non polar	33892256
L-Fucose,2TMS,isomer #3	C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C	1514.2	Semi standard non polar	33892256
L-Fucose,2TMS,isomer #4	C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O	1523.2	Semi standard non polar	33892256
L-Fucose,2TMS,isomer #5	C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C	1544.2	Semi standard non polar	33892256
L-Fucose,2TMS,isomer #6	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1504.2	Semi standard non polar	33892256
L-Fucose,3TMS,isomer #1	C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O	1572.7	Semi standard non polar	33892256
L-Fucose,3TMS,isomer #2	C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C	1582.5	Semi standard non polar	33892256
L-Fucose,3TMS,isomer #3	C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1589.1	Semi standard non polar	33892256
L-Fucose,3TMS,isomer #4	C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1581.2	Semi standard non polar	33892256
L-Fucose,4TMS,isomer #1	C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1681.3	Semi standard non polar	33892256
L-Fucose,1TBDMS,isomer #1	C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O	1720.3	Semi standard non polar	33892256
L-Fucose,1TBDMS,isomer #2	C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O	1741.2	Semi standard non polar	33892256
L-Fucose,1TBDMS,isomer #3	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	1741.1	Semi standard non polar	33892256
L-Fucose,1TBDMS,isomer #4	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	1757.7	Semi standard non polar	33892256
L-Fucose,2TBDMS,isomer #1	C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O	1987.4	Semi standard non polar	33892256
L-Fucose,2TBDMS,isomer #2	C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2014.5	Semi standard non polar	33892256
L-Fucose,2TBDMS,isomer #3	C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2016.9	Semi standard non polar	33892256
L-Fucose,2TBDMS,isomer #4	C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2008.0	Semi standard non polar	33892256
L-Fucose,2TBDMS,isomer #5	C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2029.2	Semi standard non polar	33892256
L-Fucose,2TBDMS,isomer #6	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2003.6	Semi standard non polar	33892256
L-Fucose,3TBDMS,isomer #1	C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2255.5	Semi standard non polar	33892256
L-Fucose,3TBDMS,isomer #2	C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2271.2	Semi standard non polar	33892256
L-Fucose,3TBDMS,isomer #3	C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2269.8	Semi standard non polar	33892256
L-Fucose,3TBDMS,isomer #4	C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2274.9	Semi standard non polar	33892256
L-Fucose,4TBDMS,isomer #1	C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2479.4	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Lysosome

Biospecimen Locations

Blood
Breast Milk
Feces
Saliva
Urine

Tissue Locations

Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Ovary
Pancreas
Placenta
Spleen
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Fructose and mannose metabolism	Not Available
Fructosuria		Not Available
Fructose intolerance, hereditary		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Breast Milk	Detected and Quantified	50.8908566 uM	Adult (>18 years old)	Female	Normal	11787731	details
Breast Milk	Detected and Quantified	182 +/- 135 uM	Adult (>18 years old)	Female	Normal	24027187	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	112.06 +/- 87.04 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details
Urine	Detected and Quantified	15.722 +/- 16.37 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	11.8 (6.7-26.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	9.6 (6.38-16.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	15.0 (0.0-30.0) uM	Adult (>18 years old)	Both	Cancer - assorted types	2311216	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	16.162 +/- 12.201 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Thyroid cancer
Sakai T, Yamamoto K, Yokota H, Hakozaki-Usui K, Hino F, Kato I: Rapid, simple enzymatic assay of free L-fucose in serum and urine, and its use as a marker for cancer, cirrhosis, and gastric ulcers. Clin Chem. 1990 Mar;36(3):474-6. [PubMed:2311216 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB04473

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Fucose

METLIN ID

Not Available

PubChem Compound

439554

PDB ID

Not Available

ChEBI ID

42548

Food Biomarker Ontology

Not Available

VMH ID

FUC_L

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Xu, Zuhong; Zhao, Zengqin; Zhang, Quanbin; Niu, Xizhen; Zhang, Hong; Li, Zhien. Method for preparing L-fucose from laminaria japonica. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. [PubMed:3757018 ]
Condaminet B, Peguet-Navarro J, Stahl PD, Dalbiez-Gauthier C, Schmitt D, Berthier-Vergnes O: Human epidermal Langerhans cells express the mannose-fucose binding receptor. Eur J Immunol. 1998 Nov;28(11):3541-51. [PubMed:9842897 ]
Havenaar EC, Hoff RC, van den Eijnden DH, van Dijk W: Sialyl Lewis(x) epitopes do not occur on acute phase proteins in mice: relationship to the absence of alpha3-fucosyltransferase in the liver. Glycoconj J. 1998 Apr;15(4):389-95. [PubMed:9613826 ]
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Enzymes

Enzyme Details

1. L-fucose kinase

General function:: Involved in ATP binding
Specific function:: Takes part in the salvage pathway for reutilization of fucose from the degradation of oligosaccharides.
Gene Name:: FUK
Uniprot ID:: Q8N0W3
Molecular weight:: 117621.795

Reactions

Adenosine triphosphate + L-Fucose → ADP + Fucose 1-phosphate	details

Enzyme Details

2. Acetylcholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:: ACHE
Uniprot ID:: P22303
Molecular weight:: 67795.525

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

3. Tissue alpha-L-fucosidase

General function:: Involved in alpha-L-fucosidase activity
Specific function:: Alpha-L-fucosidase is responsible for hydrolyzing the alpha-1,6-linked fucose joined to the reducing-end N-acetylglucosamine of the carbohydrate moieties of glycoproteins.
Gene Name:: FUCA1
Uniprot ID:: P04066
Molecular weight:: 53688.475

Reactions

An alpha-L-fucoside + Water → L-Fucose + an alcohol	details

Enzyme Details

4. Plasma alpha-L-fucosidase

General function:: Involved in alpha-L-fucosidase activity
Specific function:: Alpha-L-fucosidase is responsible for hydrolyzing the alpha-1,6-linked fucose joined to the reducing-end N-acetylglucosamine of the carbohydrate moieties of glycoproteins.
Gene Name:: FUCA2
Uniprot ID:: Q9BTY2
Molecular weight:: 54066.31

Reactions

An alpha-L-fucoside + Water → L-Fucose + an alcohol	details

Enzyme Details

5. Fucose mutarotase

General function:: Not Available
Specific function:: Involved in the interconversion between alpha- and beta-L-fucoses. L-Fucose (6-deoxy-L-galactose) exists as alpha-L-fucose (29.5%) and beta-L-fucose (70.5%), the beta-form is metabolized through the salvage pathway. GDP-L-fucose formed either by the de novo or salvage pathways is transported into the endoplasmic reticulum, where it serves as a substrate for N- and O-glycosylations by fucosyltransferases. Fucosylated structures expressed on cell surfaces or secreted in biological fluids are believed to play a critical role in cell-cell adhesion and recognition processes.
Gene Name:: FUOM
Uniprot ID:: A2VDF0
Molecular weight:: 16764.555

Reactions

L-Fucose → beta-L-Fucose	details

Showing metabocard for L-Fucose (HMDB0000174)

MOL for HMDB0000174 (L-Fucose)

3D MOL for HMDB0000174 (L-Fucose)

3D SDF for HMDB0000174 (L-Fucose)

3D-SDF for HMDB0000174 (L-Fucose)

PDB for HMDB0000174 (L-Fucose)

3D PDB for HMDB0000174 (L-Fucose)

SMILES for HMDB0000174 (L-Fucose)

INCHI for HMDB0000174 (L-Fucose)

Structure for HMDB0000174 (L-Fucose)

3D Structure for HMDB0000174 (L-Fucose)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

References

Reactions

Reactions

Reactions