Elfucose

Elfucose

Cas 87-96-7

Chemical Formula: C6H12O5
Exact Mass: 164.07
Molecular Weight: 164.157

L-fucopyranose (6-deoxy-L-galactopyranose)

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

• 6-Deoxy-L-galactose (ACI)
• Fucose, L- (8CI)
• (-)-Fucose
• 46: PN: US20220380460 SEQID: 47 claimed sequence
• 6-Desoxygalactose
• L-(-)-Fucose
• L-Fucose
• L-Galactomethylose
• L-Galactopyranose, 6-deoxy-
• CERC 803
• Elfucose
• Fucose
• NSC 1219
• congenital glycosylation disorders
• 6-Deoxy-L-galactopyranose
• L-galactomethylose
• 87-96-7
• Fucose, L-
• 6-deoxy-galactose

Fucose is under investigation in clinical trial NCT03354533 (Study of ORL-1F (L-fucose) in Patients With Leukocyte Adhesion Deficiency Type II).

L-fucopyranose is the pyranose form of L-fucose. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a L-fucose and a fucopyranose.

SCHEME

PATENT

054381301,

JP2000125857A1,

JP2003231694A5,

JP2008120707A1,

JP5327642B21,

JPH00690765A1,

JPH07115968A1,

JPH07184647A1,

JPH08242876A1,

JPH1135591A1,

JPH1160593A1

PATENT

WO2016150629

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2016150629&_cid=P10-MB1MYE-34318-1

Examples

The invention will now be illustrated in more detail by the following non-limiting examples.

Example 1: Production of L-fucose by biocatalytic oxidation of L-fucitol with galactose oxidase in the presence of peroxidase and catalase

A solution of L-fucitol (6.0 mL aqueous solution containing 600 mg L-fucitol, CAS 13074-06-1, Santa Cruz Biotechnology) was added to a round-bottom three-neck bottle (50 mL), followed by the addition of 1.2 mL K2HPO4 _/ KH2PO4 _( 1000 mM , pH=7.0) and 0.095 mL catalase (from bovine liver, SIGMA, 21,300 U/mg, 34 mg/mL), 0.120 mL peroxidase (from horseradish, 173 U/mg solid, SIGMA ) and 2.218 mL galactose oxidase (38.4 mg/mL, 2,708 U/mL). The resulting solution was purged with O ₂ at room temperature until all L-fucitol was converted to L-fucose. The reaction was monitored by HLPC. The final product was isolated and analyzed by 1 H and 13C NMR. The results are summarized in Table 1.

[Table 1]

Reaction time [h] Conversion [%]

0

3,5 54,0

24 95,8

29 96,0

PATENT

WO2010022244

WO2007021879

////////////Elfucose, 6-Deoxy-L-galactose, Fucose, L- , (-)-Fucose, 6-Desoxygalactose, L-(-)-Fucose, L-Fucose, L-Galactomethylose, L-Galactopyranose, 6-deoxy-, CERC 803, Elfucose, Fucose, NSC 1219, congenital glycosylation disorders, 6-Deoxy-L-galactopyranose, L-galactomethylose, 87-96-7, Fucose, L-, 6-deoxy-galactose