118396-37-5

Upstream product

• 447-25-6 6-deoxy-6-fluoro-D-galactopyranose 
• 108-24-7 acetic anhydride 
• 3396-99-4 methyl α-D-galactopyranoside 
• 4536-13-4 methyl 6-deoxy-6-fluoro-α-D-galactopyranoside 
• 2021-97-8 6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-D-galctopyranose 

Downstream Products

• 144220-97-3 2,4-dinitrophenyl-6-fluoro-6-deoxy-β-D-galactopyranoside 
• 1191118-29-2 N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2-deoxy-4,6-O-benzylidene-3-O-[2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranosyl])-α-D-galactopyranosyl-L-threonine-tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of fluorinated analogues of tumor-associated carbohydrate and glycopeptide antigens

Partial structures of tumor-associated mucin glycoproteins are interesting target structures for the development of selective anticancer vaccines. To probe the effect of fluorination on the immunological and metabolic properties of mucin glycopeptides, six novel fluorinated glycosyl-threonine conjugates have been synthesized. The synthesis of the orthogonally protected glycosyl amino acids was achieved using microwave irradiation in key fluorination and glycosylation steps. The 2′-deoxy-2′-fluoro- and 6′-deoxy-6′-fluoro-T antigen building blocks were applied to the synthesis of analogues of MUC1 tandem repeat-glycopeptide antigens via SPPS. Georg Thieme Verlag Stuttgart.

UDP-6-deoxy-6-fluoro-α-D-galactose binds to two different galactosyltransferases, but neither can effectively catalyze transfer of the modified galactose to the appropriate acceptor

The effect of substitution of the HO-6 of D-galactose with fluorine on the ability of α-(1→3)-galactosyltransferase (EC 2.4.1.151) and β-(1→4)-galactosyltransferase (EC 2.4.1.22) to catalyze its transfer from UDP to an appropriate acceptor was determined. HPLC analyses indicated that each transferase properly catalyzed formation of the expected product [β-D-Gal-(1→4)-D-GlcNAc] for the β-(1→4)-galactosyltransferase and α-D-Gal-(1→3)-β-D-Gal-(1→4)-D-GlcNAc for the α-(1→3)-D-galactosyltransferase] when UDP-α-D-Gal was the substrate. When UDP-6-deoxy-6-fluoro-α-D-galactose (6) was used in conjunction with each transferase, no product indicative of transfer of 6-deoxy-6-fluoro-D-galactose to its respective acceptor sugar was identified. 6-Deoxy-6-fluoro-D-galactose (3) was obtained by hydrolysis of methyl 6-deoxy-6-fluoro-α-D-galactopyranoside, synthesized by the selective fluorination of methyl α-D-galactopyranoside with diethylaminosulfur trifluoride (DAST), with aqueous trifluoroacetic acid. Acetylation of 3 gave crystalline 1,2,3,4-tetra-O-acetyl-6-deoxy-6-fluoro-β-D-galactopyranose, which was converted to the corresponding 1-α-phosphate and used for the synthesis of 6. Copyright (C) 1999 Elsevier Science Ltd.