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MedKoo Cat#: 597082 | Name: Fucosamine

Description:

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

Fucosamine is an amino sugar derived from fucose.

Chemical Structure

Fucosamine
Fucosamine
CAS#7577-62-0

Theoretical Analysis

MedKoo Cat#: 597082

Name: Fucosamine

CAS#: 7577-62-0

Chemical Formula: C6H13NO4

Exact Mass: 163.0845

Molecular Weight: 163.17

Elemental Analysis: C, 44.17; H, 8.03; N, 8.58; O, 39.22

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.
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Related CAS #
No Data
Synonym
Fucosamine;
IUPAC/Chemical Name
(2S,3S,4R,5S)-2-amino-3,4,5-trihydroxyhexanal
InChi Key
NTBYIQWZAVDRHA-KCDKBNATSA-N
InChi Code
InChI=1S/C6H13NO4/c1-3(9)5(10)6(11)4(7)2-8/h2-6,9-11H,7H2,1H3/t3-,4+,5+,6-/m0/s1
SMILES Code
O=C[C@@H](N)[C@@H]([C@@H]([C@H](C)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

Preparing Stock Solutions

The following data is based on the product molecular weight 163.17 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.

Recalculate based on batch purity %
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
1: Flamm D, Blaschek W. Exopolysaccharides of Synechocystis aquatilis are sulfated arabinofucans containing N-acetyl-fucosamine. Carbohydr Polym. 2014 Jan 30;101:301-6. doi: 10.1016/j.carbpol.2013.09.036. Epub 2013 Sep 21. PubMed PMID: 24299777. 2: Leonori D, Seeberger PH. De novo synthesis of D- and L-fucosamine containing disaccharides. Beilstein J Org Chem. 2013;9:332-41. doi: 10.3762/bjoc.9.38. Epub 2013 Feb 14. PubMed PMID: 23503315; PubMed Central PMCID: PMC3596053. 3: Leonori D, Seeberger PH. De novo synthesis of the bacterial 2-amino-2,6-dideoxy sugar building blocks D-fucosamine, D-bacillosamine, and D-xylo-6-deoxy-4-ketohexosamine. Org Lett. 2012 Sep 21;14(18):4954-7. Epub 2012 Sep 6. PubMed PMID: 22954071. 4: Hung MN, Rangarajan E, Munger C, Nadeau G, Sulea T, Matte A. Crystal structure of TDP-fucosamine acetyltransferase (WecD) from Escherichia coli, an enzyme required for enterobacterial common antigen synthesis. J Bacteriol. 2006 Aug;188(15):5606-17. PubMed PMID: 16855251; PubMed Central PMCID: PMC1540030. 5: Mulrooney EF, Poon KK, McNally DJ, Brisson JR, Lam JS. Biosynthesis of UDP-N-acetyl-L-fucosamine, a precursor to the biosynthesis of lipopolysaccharide in Pseudomonas aeruginosa serotype O11. J Biol Chem. 2005 May 20;280(20):19535-42. Epub 2005 Mar 18. PubMed PMID: 15778500. 6: Druzhinina TN, Kalinchuk NA, Shibaev VN. Biosynthesis of uridine diphosphate N-acetyl-L-fucosamine in a cell-free system from Salmonella arizonae O:59. Biochemistry (Mosc). 2005 Jan;70(1):85-91. PubMed PMID: 15701053. 7: Kneidinger B, O'Riordan K, Li J, Brisson JR, Lee JC, Lam JS. Three highly conserved proteins catalyze the conversion of UDP-N-acetyl-D-glucosamine to precursors for the biosynthesis of O antigen in Pseudomonas aeruginosa O11 and capsule in Staphylococcus aureus type 5. Implications for the UDP-N-acetyl-L-fucosamine biosynthetic pathway. J Biol Chem. 2003 Feb 7;278(6):3615-27. Epub 2002 Dec 2. PubMed PMID: 12464616. 8: Vinogradov EV, Kaca W, Knirel YA, Rózalski A, Kochetkov NK. Structural studies on the fucosamine-containing O-specific polysaccharide of Proteus vulgaris O19. Eur J Biochem. 1989 Mar 1;180(1):95-9. PubMed PMID: 2651127. 9: Aono R, Uramoto M. Presence of fucosamine in teichuronic acid of the alkalophilic Bacillus strain C-125. Biochem J. 1986 Jan 1;233(1):291-4. PubMed PMID: 3006662; PubMed Central PMCID: PMC1153020. 10: Yaguchi M, Daoust V, Perry MB. Ion-exchange chromatography of 2-amino-2,6-dideoxyhexoses and of the methyl ethers of 2-amino-2,6-dideoxy-D-glucopyranose (quinovosamine) and 2-amino-2,6-dideoxy-D-galactopyranose (fucosamine). Carbohydr Res. 1975 Jan;39(1):131-5. PubMed PMID: 1111960. 11: Liau DF, Melly MA, Hash JH. Surface polysaccharide from Staphylococcus aureus M that contains taurine, D-aminogalacturonic acid, and D-fucosamine. J Bacteriol. 1974 Sep;119(3):913-22. PubMed PMID: 4854538; PubMed Central PMCID: PMC245699. 12: Suzuki N. [Isolation of DL-fucosamine from Pseudomonus aeruginosa N10]. Seikagaku. 1969 Nov;41(11):769-76. Japanese. PubMed PMID: 4983110. 13: Suzuki N. Isolation of DL-fucosamine from Pseudomonas aeruginosa N10. Biochim Biophys Acta. 1969 Apr 1;177(2):371-3. PubMed PMID: 4976289. 14: Erler W. [Serological, chemical and immunochemical studies on the swine erysipelas bacterium. IV. Occurrence of fucosamine (2,6-didesoxy-2-aminogalactose) in the swine erysipelas bacterium]. Arch Exp Veterinarmed. 1968;22(6):1155-63. German. PubMed PMID: 5754076. 15: Sharon N, Shif I, Zehavi U. The isolation of D-fucosamine (2-amino-2,6-dideoxy-D-galactose) from polysaccharides of Bacillus. Biochem J. 1964 Oct;93(1):210-4. PubMed PMID: 4953793; PubMed Central PMCID: PMC1206202. 16: BARRY GT, ROARK E. L-FUCOSAMINE AND 4-OXO-NORLEUCINE AS CONSTITUENTS IN MUCOPOLYSACCHARIDES OF CERTAIN ENTERIC BACTERIA. Nature. 1964 May 2;202:493-4. PubMed PMID: 14167835. 17: WHEAT R, ROLLINS EL, LEATHERWOOD J. ISOLATION OF D-FUCOSAMINE FROM BACILLUS CEREUS. Nature. 1964 May 2;202:492-3. PubMed PMID: 14167834. 18: CRUMPTON MJ, DAVIES DA. The isolation of D-fucosamine from the specific polysaccharide of Chromobacterium violaceum (NCTC 7917). Biochem J. 1958 Dec;70(4):729-36. PubMed PMID: 13607435; PubMed Central PMCID: PMC1196734.