L-Fucose | CAS#2438-80-4 | sugar

MedKoo Cat#: 597072 | Name: L-Fucose

Description:

WARNING: This product is for research use only, not for human or veterinary use.

L-Fucose is a six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule.

Chemical Structure

L-Fucose

CAS#2438-80-4

Theoretical Analysis

MedKoo Cat#: 597072

Name: L-Fucose

CAS#: 2438-80-4

Chemical Formula: C6H12O5

Exact Mass: 164.0685

Molecular Weight: 164.16

Elemental Analysis: C, 43.90; H, 7.37; O, 48.73

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

L-Fucose; (-)-L-Fucose; Fucosse; 6-Desoxygalactose;

IUPAC/Chemical Name

(2R,3R,4S,5R,6R)-6-methyltetrahydro-2H-pyran-2,3,4,5-tetraol

InChi Key

SHZGCJCMOBCMKK-FPRJBGLDSA-N

InChi Code

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

SMILES Code

O[C@H]1[C@@H]([C@H]([C@H]([C@@H](C)O1)O)O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

(-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.

In vitro activity:

Further studies showed that L-fucose promoted IL-22 release from CD4+ T cells and intestinal lamina propria monocytes (LPMCs) via activation of nuclear AHR. The coculture system of LPMCs and intestinal organoids demonstrated that L-fucose stimulated the proliferation of ISCs through an indirect manner of IL-22 from LPMCs via the IL-22R-p-STAT3 pathway, and restored TNF-α-induced organoid damage via IL-22-IL-22R signaling. Reference: Nutrients. 2022 Nov 12;14(22):4789. https://pubmed.ncbi.nlm.nih.gov/36432480/

In vivo activity:

This study found that in Muc2-/- mice L-fucose reduced macrophage infiltration and IL-1a, TNFa, IFNgamma, IL-6, MCP-1, RANTES, MIP1b levels, decreased Nos2 expression, and induced the expression of Treg marker Foxp3 gene. This study demonstrated that anti-inflammatory effect of L-fucose observed in Muc2-/- mice is not reproduced in PrkdcSCIDMuc2-/-, which lack lymphocytes.

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	121.83
	DMSO	40.0	243.67
	Ethanol	0.3	1.83
	PBS (pH 7.2)	10.0	60.92
	Water	100.0	609.17

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 164.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Tan C, Hong G, Wang Z, Duan C, Hou L, Wu J, Qian W, Han C, Hou X. Promoting Effect of L-Fucose on the Regeneration of Intestinal Stem Cells through AHR/IL-22 Pathway of Intestinal Lamina Propria Monocytes. Nutrients. 2022 Nov 12;14(22):4789. doi: 10.3390/nu14224789. PMID: 36432480; PMCID: PMC9695883. 2. Duan C, Tang X, Wang W, Qian W, Fu X, Deng X, Han C, Hou X. L-fucose ameliorates the carcinogenic properties of Fusobacterium nucleatum in colorectal cancer. Oncol Lett. 2021 Feb;21(2):143. doi: 10.3892/ol.2020.12404. Epub 2020 Dec 21. PMID: 33552262; PMCID: PMC7798039. 3. Feofanova NA, Bets VD, Borisova MA, Litvinova EA. L-fucose reduces gut inflammation due to T-regulatory response in Muc2 null mice. PLoS One. 2022 Dec 30;17(12):e0278714. doi: 10.1371/journal.pone.0278714. PMID: 36584066; PMCID: PMC9803192. 4. Achasova KM, Kozhevnikova EN, Borisova MA, Litvinova EA. Fucose Ameliorates Tritrichomonas sp.-Associated Illness in Antibiotic-Treated Muc2-/- Mice. Int J Mol Sci. 2021 Oct 2;22(19):10699. doi: 10.3390/ijms221910699. PMID: 34639039; PMCID: PMC8509520.

In vitro protocol:

In vivo protocol:

1. Feofanova NA, Bets VD, Borisova MA, Litvinova EA. L-fucose reduces gut inflammation due to T-regulatory response in Muc2 null mice. PLoS One. 2022 Dec 30;17(12):e0278714. doi: 10.1371/journal.pone.0278714. PMID: 36584066; PMCID: PMC9803192. 2. Achasova KM, Kozhevnikova EN, Borisova MA, Litvinova EA. Fucose Ameliorates Tritrichomonas sp.-Associated Illness in Antibiotic-Treated Muc2-/- Mice. Int J Mol Sci. 2021 Oct 2;22(19):10699. doi: 10.3390/ijms221910699. PMID: 34639039; PMCID: PMC8509520.

1: Shoemaker CA, LaFrentz BR, Peatman E, Beck BH. Influence of native catfish mucus on Flavobacterium columnare growth and proteolytic activity. J Fish Dis. 2018 Jun 11. doi: 10.1111/jfd.12833. [Epub ahead of print] PubMed PMID: 29893005. 2: McKenzie NC, Scott NE, John A, White JM, Goddard-Borger ED. Synthesis and use of 6,6,6-trifluoro-L-fucose to block core-fucosylation in hybridoma cell lines. Carbohydr Res. 2018 May 23;465:4-9. doi: 10.1016/j.carres.2018.05.008. [Epub ahead of print] PubMed PMID: 29874559. 3: Yu J, Shin J, Park M, Seydametova E, Jung SM, Seo JH, Kweon DH. Engineering of α-1,3-fucosyltransferases for production of 3-fucosyllactose in Escherichia coli. Metab Eng. 2018 Jun 2. pii: S1096-7176(17)30465-2. doi: 10.1016/j.ymben.2018.05.021. [Epub ahead of print] PubMed PMID: 29870790. 4: Abronina PI, Zinin AI, Romashin DA, Tereshina VV, Chizhov AO, Kononov LO. Application of a Janus aglycon with dual function in benzyl-free synthesis of spacer-armed oligosaccharide fragments of polysaccharides from rhizobacterium Azospirillum brasilense sp7. Carbohydr Res. 2018 Jul 15;464:28-43. doi: 10.1016/j.carres.2018.05.005. Epub 2018 May 16. PubMed PMID: 29803733. 5: Gui C, Yuan J, Mo X, Huang H, Zhang S, Gu YC, Ju J. Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces. J Nat Prod. 2018 May 25;81(5):1278-1289. doi: 10.1021/acs.jnatprod.8b00212. Epub 2018 May 16. PubMed PMID: 29767975. 6: Uemura R, Ogura M, Matsumaru C, Akiyama T, Maeda M, Kimura Y. Novel assay system for acidic Peptide:N-glycanase (aPNGase) activity in crude plant extract. Biosci Biotechnol Biochem. 2018 Apr 15:1-4. doi: 10.1080/09168451.2018.1459464. [Epub ahead of print] PubMed PMID: 29658432. 7: Kurakake M, Amai Y, Konishi M, Ikehira K. Characteristics of an β-N-Acetylhexosaminidase from Bacillus sp. CH11, Including its Transglycosylation Activity. J Food Sci. 2018 May;83(5):1208-1214. doi: 10.1111/1750-3841.14125. Epub 2018 Apr 6. PubMed PMID: 29624688. 8: Ibrahim D. Glycoconjugates pattern and chemosensory cells in the camel respiratory mucosa: Lectin and immunohistochemical studies. Tissue Cell. 2018 Apr;51:84-90. doi: 10.1016/j.tice.2018.03.006. Epub 2018 Mar 12. PubMed PMID: 29622093. 9: Naumenko OI, Zheng H, Xiong Y, Senchenkova SN, Wang H, Shashkov AS, Li Q, Wang J, Knirel YA. Studies on the O-polysaccharide of Escherichia albertii O2 characterized by non-stoichiometric O-acetylation and non-stoichiometric side-chain l-fucosylation. Carbohydr Res. 2018 May 22;461:80-84. doi: 10.1016/j.carres.2018.02.013. Epub 2018 Mar 6. PubMed PMID: 29609101. 10: Diesner SC, Bergmayr C, Wang XY, Heiden D, Exenberger S, Roth-Walter F, Starkl P, Ret D, Pali-Schöll I, Gabor F, Untersmayr E. Characterization of Vibrio cholerae neuraminidase as an immunomodulator for novel formulation of oral allergy immunotherapy. Clin Immunol. 2018 Jul;192:30-39. doi: 10.1016/j.clim.2018.03.017. Epub 2018 Mar 30. PubMed PMID: 29608970; PubMed Central PMCID: PMC6002774. 11: Perrella NN, Fuzita FJ, Moreti R, Verhaert PDEM, Lopes AR. First characterization of fucosidases in spiders. Arch Insect Biochem Physiol. 2018 Jul;98(3):e21462. doi: 10.1002/arch.21462. Epub 2018 Mar 30. PubMed PMID: 29600526. 12: Vineethkumar TV, Shyla G, George S. Smallest lectin-like peptide identified from the skin secretion of an endemic frog, Hydrophylax bahuvistara. Acta Biol Hung. 2018 Mar;69(1):110-113. doi: 10.1556/018.68.2018.1.9. PubMed PMID: 29575918. 13: Wang HT, Yang LC, Yu HC, Chen ML, Wang HJ, Lu TJ. Characteristics of fucose-containing polysaccharides from submerged fermentation of Agaricus blazei Murill. J Food Drug Anal. 2018 Apr;26(2):678-687. doi: 10.1016/j.jfda.2017.07.006. Epub 2017 Aug 18. PubMed PMID: 29567238. 14: Wang Y, Liu M, Liu L, Xia JH, Du YG, Sun JS. The Structural Revision and Total Synthesis of Carambolaflavone A. J Org Chem. 2018 Apr 6;83(7):4111-4118. doi: 10.1021/acs.joc.8b00008. Epub 2018 Mar 13. PubMed PMID: 29504402. 15: Zhao L, Qin Y, Guan R, Zheng W, Liu J, Zhao J. Digestibility of fucosylated glycosaminoglycan from sea cucumber and its effects on digestive enzymes under simulated salivary and gastrointestinal conditions. Carbohydr Polym. 2018 Apr 15;186:217-225. doi: 10.1016/j.carbpol.2018.01.029. Epub 2018 Jan 11. PubMed PMID: 29455981. 16: Wang WH, Zhang JS, Feng T, Deng J, Lin CC, Fan H, Yu WJ, Bao HY, Jia W. Structural elucidation of a polysaccharide from Flammulina velutipes and its immunomodulation activities on mouse B lymphocytes. Sci Rep. 2018 Feb 15;8(1):3120. doi: 10.1038/s41598-018-21375-0. PubMed PMID: 29449636; PubMed Central PMCID: PMC5814432. 17: Cattiaux L, Porkolab V, Fieschi F, Mallet JM. New branched amino acids for high affinity dendrimeric DC-SIGN ligands. Bioorg Med Chem. 2018 Mar 1;26(5):1006-1015. doi: 10.1016/j.bmc.2017.12.036. Epub 2017 Dec 26. PubMed PMID: 29428526. 18: Wands AM, Cervin J, Huang H, Zhang Y, Youn G, Brautigam CA, Matson Dzebo M, Björklund P, Wallenius V, Bright DK, Bennett CS, Wittung-Stafshede P, Sampson NS, Yrlid U, Kohler JJ. Fucosylated Molecules Competitively Interfere with Cholera Toxin Binding to Host Cells. ACS Infect Dis. 2018 May 11;4(5):758-770. doi: 10.1021/acsinfecdis.7b00085. Epub 2018 Feb 22. PubMed PMID: 29411974; PubMed Central PMCID: PMC5948155. 19: Roy G, Martin T, Barnes A, Wang J, Jimenez RB, Rice M, Li L, Feng H, Zhang S, Chaerkady R, Wu H, Marelli M, Hatton D, Zhu J, Bowen MA. A novel bicistronic gene design couples stable cell line selection with a fucose switch in a designer CHO host to produce native and afucosylated glycoform antibodies. MAbs. 2018 Apr;10(3):416-430. doi: 10.1080/19420862.2018.1433975. Epub 2018 Feb 22. PubMed PMID: 29400603; PubMed Central PMCID: PMC5916560. 20: Gonçalves B, Sechet J, Arnaud N. Xyloglucans fucosylation defects do not alter plant boundary domain definition. Plant Signal Behav. 2018 Feb 1;13(2):e1430545. doi: 10.1080/15592324.2018.1430545. Epub 2018 Feb 6. PubMed PMID: 29351054; PubMed Central PMCID: PMC5846562.