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F1395

Sigma-Aldrich

β-L-Fucose 1-phosphate bis(cyclohexylammonium) salt

≥98%

Synonym(s):

6-Deoxy-β-L-galactose 1-phosphate

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About This Item

Empirical Formula (Hill Notation):
C6H11O8P · 2C6H14N
Molecular Weight:
442.48
MDL number:
MFCD22681514
UNSPSC Code:
12352201
PubChem Substance ID:
329799679
NACRES:
NA.25

Quality Level

100

Assay

≥98%

form

powder

technique(s)

thin layer chromatography (TLC): suitable

solubility

H2O: soluble 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

NC1CCCCC1.NC2CCCCC2.C[C@@H]3O[C@H](OP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]3O

InChI

1S/2C6H13N.C6H13O8P/c2*7-6-4-2-1-3-5-6;1-2-3(7)4(8)5(9)6(13-2)14-15(10,11)12/h2*6H,1-5,7H2;2-9H,1H3,(H2,10,11,12)/t;;2-,3+,4+,5-,6+/m..0/s1

InChI key

FQMPFZHILABVMA-PEJHDPODSA-N

Application

β-L-Fucose 1-phosphate is suitable as both substrate and product to identify, differentiate and characterize GTP fucose pyrophosphorylase(s) (GFPP; fucose-1-phosphate guanylyltransferases) involved in the formation of the nucleotide-sugar GDP-beta-l-fucose and other fucosylation donor substrates such as 3,3′-Diaminobenzidine (GDP)-β-l-fucose. β-L-Fucose 1-phosphate may be used to generate new fucosylation donor substrates for use in glycan fucosylation research.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Toshihisa Kotake et al.
The Journal of biological chemistry, 283(13), 8125-8135 (2008-01-18)
Monomeric sugars generated during the metabolism of polysaccharides, glycoproteins, and glycolipids are imported to the cytoplasm and converted to respective nucleotide sugars via monosaccharide 1-phosphates, to be reutilized as activated sugars. Because L-fucose (L-Fuc) is activated mainly in the form
GDP-L-fucose pyrophosphorylase. Purification, cDNA cloning, and properties of the enzyme.
Pastuszak I, Ketchum C, Hermanson G, et al.
The Journal of Biological Chemistry, 4273, 30165-30174 (1998)
Bing Ma et al.
Glycobiology, 16(12), 158R-184R (2006-09-16)
Fucosylated carbohydrate structures are involved in a variety of biological and pathological processes in eukaryotic organisms including tissue development, angiogenesis, fertilization, cell adhesion, inflammation, and tumor metastasis. In contrast, fucosylation appears less common in prokaryotic organisms and has been suggested
Stephen Quirk et al.
Biochemistry, 44(32), 10854-10863 (2005-08-10)
GTP-l-fucose pyrophosphorylase (GFPP, E. C. 2.7.7.30) catalyzes the reversible condensation of guanosine triphosphate and beta-l-fucose-1-phosphate to form the nucleotide-sugar GDP-beta-l-fucose. The enzyme functions primarily in the mammalian liver and kidney to salvage free l-fucose during the breakdown of glycolipids and
Leonie Engels et al.
Glycobiology, 24(2), 170-178 (2013-11-20)
Fucosyltransferases (FucTs) are essential tools for the synthesis of fucosylated glycoconjugates. Multistep enzyme catalysis of fucosylated glycans is not limited as long as isolated and well-characterized FucTs are available. The present paper introduces a novel bacterial α1,2-FucT of the glycosyltransferase
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