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F2252

Sigma-Aldrich

L-(−)-Fucose

≥98% (GC)

Synonym(s):

6-Deoxy-L-galactose

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About This Item

Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
2438-80-4
Molecular Weight:
164.16
Beilstein:
1723321
EC Number:
219-452-7
MDL number:
MFCD00135607
UNSPSC Code:
12352201
PubChem Substance ID:
24894816
NACRES:
NA.25
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Quality Level

200

Assay

≥98% (GC)

form

powder

technique(s)

gas chromatography (GC): suitable

color

white

mp

150-153 °C (lit.)

solubility

H2O: soluble 50 mg/mL, clear to very slightly hazy

SMILES string

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

InChI

1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4+,5+,6-/m0/s1

InChI key

PNNNRSAQSRJVSB-KCDKBNATSA-N

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General description

L-Fucose, a natural monosaccharide found in mammals, is an important component of several N- and O-linked glycans and glycolipids.

Application

L-(−)-Fucose has been used:
  • as the non-haptenic sugar in lectin bead-binding assay to study its effects on the binding of immobilized lectins like peanut agglutinin (PNA) and Dolichos biflorus agglutinin (DBA)
  • as an internal standard to dilute the enzymatic hydrolysates for analytical methods
  • in the synthesis of fucosyl thioglycoside

Biochem/physiol Actions

L-Fucose (6-Deoxy-L-galactose) is used in studies of fucoidan polysaccharides containing glycans. It is studied as a glycan modifying carbohydrate that generates antigenic sites recognized by IgE antibodies. L-Fucose is used as a substrate to identify, differentiate, and characterize enzymes such as fucosidase(s),l-fucose isomerase(s), and L-fucose dehydrogenase(s). It may be used to study organelles, and bacterial microcompartments, involved in the degradation of plant and algal cell wall sugars. L-Fucose may also be used as a reference compound in rare sugar identification and analysis.
L-Fucose is broadly used as a food additive. It possesses anti-inflammatory effects. It can inhibit the cutaneous immune reaction and alveolar macrophage priming. L-fucose can also suppress tumor growth and tumorigenesis.

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000406280
0000406280
0000403543
0000379658
0000379648

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Barbara Bolgiano et al.
Pathogens (Basel, Switzerland), 10(8) (2021-08-29)
Towards achieving the goal of eliminating epidemic outbreaks of meningococcal disease in the African meningitis belt, a pentavalent glycoconjugate vaccine (NmCV-5) has been developed to protect against Neisseria meningitidis serogroups A, C, Y, W and X. MenA and X polysaccharides
Jing-Jing Liu et al.
Biotechnology and bioengineering, 116(4), 904-911 (2019-01-01)
L-Fucose (6-deoxy-L-galactose) is a major constituent of glycans and glycolipids in mammals. Fucosylation of glycans can confer unique functional properties and may be an economical way to manufacture L-fucose. Research can extract L-fucose directly from brown algae, or by enzymatic
Karineh Petrossian et al.
Acta histochemica, 109(6), 491-500 (2007-08-21)
By using a non-cancer and a cancer cell line originally from the same tissue (colon), coupled with testing lectins for cell binding and for their effects on these cell lines in culture, this study describes a simple multi-parameter approach that
Krzysztof Brzezinski et al.
Acta crystallographica. Section D, Biological crystallography, 68(Pt 2), 160-168 (2012-01-28)
Rhizobial NodZ α1,6-fucosyltransferase (α1,6-FucT) catalyzes the transfer of the fucose (Fuc) moiety from guanosine 5'-diphosphate-β-L-fucose to the reducing end of the chitin oligosaccharide core during Nod-factor (NF) biosynthesis. NF is a key signalling molecule required for successful symbiosis with a
Feng Gu et al.
Bioresource technology, 149, 375-382 (2013-10-17)
Green liquor (Na2S+Na2CO3, GL) pretreatment is a proven pathway to improve the enzymatic saccharification for the production of bioethanol. In this work, the effects of GL pretreatment on the chemical composition and enzymatic digestibility of rice straw at various total
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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