188783-78-0

Basic information

• Product Name: 1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucose
• Synonyms: 1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucose;2,6-Dideoxy-2-fluoro-L-galactopyranose triacetate;2,6-Dideoxy-2-fluoro-L-galactopyranose 1,3,4-Triacetate;[(2S,3R,4R,5S)-4,6-Diacetoxy-5-fluoro-2-methyl-tetrahydropyran-3-yl] acetate;(3S,4R,5R,6S)-3-fluoro-6-methyl-tetrahydro-2H-pyran-2,4,5-triyl triacetate
• CAS NO: 188783-78-0
• Molecular Formula: C12H17FO7
• Molecular Weight: 292.2575832
• Mol File: 188783-78-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucose(188783-78-0)
• EPA Substance Registry System: 1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucose(188783-78-0)

Safety Data

• Hazardous Substances Data: 188783-78-0(Hazardous Substances Data)

Usage

Uses

2,6-Dideoxy-2-fluoro-L-galactopyranose 1,3,4-Triacetate is a reactant in the preparation of β-purine-diphosphate sugars (GDP-fucose-analogs)

Upstream product

• 64-19-7 acetic acid 
• 54621-94-2 3,4-di-O-acetyl-L-fucal 
• 108-24-7 acetic anhydride 
• 74554-10-2 3,4-di-O-acetyl-2-deoxy-2-fluoro-α-L-fucopyranosyl fluoride 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 73-34-7 6-deoxy-L-galactose 

Downstream Products

• 188783-82-6 (3,4-Di-O-acetyl-2-deoxy-2-fluoro-β-L-fucopyranosyl) dibenzyl phosphate 

Relevant articles and documents

Designer α1,6-Fucosidase Mutants Enable Direct Core Fucosylation of Intact N-Glycopeptides and N-Glycoproteins

Core fucosylation of N-glycoproteins plays a crucial role in modulating the biological functions of glycoproteins. Yet, the synthesis of structurally well-defined, core-fucosylated glycoproteins remains a challenging task due to the complexity in multistep chemical synthesis or the inability of the biosynthetic α1,6-fucosyltransferase (FUT8) to directly fucosylate full-size mature N-glycans in a chemoenzymatic approach. We report in this paper the design and generation of potential α1,6-fucosynthase and fucoligase for direct core fucosylation of intact N-glycoproteins. We found that mutation at the nucleophilic residue (D200) did not provide a typical glycosynthase from this bacterial enzyme, but several mutants with mutation at the general acid/base residue E274 of the Lactobacillus casei α1,6-fucosidase, including E274A, E274S, and E274G, acted as efficient glycoligases that could fucosylate a wide variety of complex N-glycopeptides and intact glycoproteins by using α-fucosyl fluoride as a simple donor substrate. Studies on the substrate specificity revealed that the α1,6-fucosidase mutants could introduce an α1,6-fucose moiety specifically at the Asn-linked GlcNAc moiety not only to GlcNAc-peptide but also to high-mannose and complex-type N-glycans in the context of N-glycopeptides, N-glycoproteins, and intact antibodies. This discovery opens a new avenue to a wide variety of homogeneous, core-fucosylated N-glycopeptides and N-glycoproteins that are hitherto difficult to obtain for structural and functional studies.

METHODS AND COMPOSITIONS FOR MAKING ANTIBODIES AND ANTIBODY DERIVATIVES WITH REDUCED CORE FUCOSYLATION

The invention provides methods and compositions for preparing antibodies and antibody derivatives with reduced core fucosylation.

Process for preparing nucleotide inhibitors of glycosyltransferases

Nucleotide linked 2-deoxy-2-fluoroglycosides are employed as potent competitive inhibitors of glycosyltransferases. More particularly, uridine-5'-diphospho-2-deoxy-2-fluoro-galactose (UDP-2F-Gal), guanidine-5'-diphospho-2-deoxy-2-fluoro-L-fucose (GDP-2F-Fuc), uridine-51-diphospho-2-deoxy-2-fluoro-D-glucose (UDP-2F-Glu), guanosine-5'-diphospho-2-deoxy-2-fluoro-D-mannose (GDP-2F-Man), cytosine-5'-monophospho-2-deoxy-2-fluoro-D-sialic acid, and cytosine-5'-monophospho-2-deoxy-2-KDO may be employed as inhibitors of β-1,4-galactosyltransferase, α-1,3-fucosyltransferase, glucosyltransferases, N-acetylglucosaminyltransferases, (α-mannosyltransferases, α-sialyltransferases, and KDO-transferases, respectively. Synthesis of nucleotide-linked-2-deoxy-2-fluoroglycosides is achieved using either chemoenzymatic or chemical methodologies.