Improved chemical synthesis of UDP-galactofuranose.

[reaction: see text] A reliable and efficient synthetic route to UDP-alpha-D-galactofuranose (UDP-Galf) has been developed. Reaction of UMP-N-methylimidazolide with Galf 1-phosphate proceeds rapidly to provide UDP-Galf with excellent reproducibility and in a yield approximately twice as high as those reported previously.

[1]  G. Besra,et al.  Biosynthesis of the Galactan Component of the Mycobacterial Cell Wall* , 2000, The Journal of Biological Chemistry.

[2]  Hung‐wen Liu,et al.  Studies of UDP-Galactopyranose Mutase from Escherichia coli: An Unusual Role of Reduced FAD in Its Catalysis , 2000 .

[3]  A. Nikolaev,et al.  The first chemical synthesis of UDP-α-D-galactofuranose , 2000 .

[4]  Chi‐Huey Wong,et al.  1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions: Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose. , 1997, The Journal of organic chemistry.

[5]  J. Brisson,et al.  UDP-galactofuranose Precursor Required for Formation of the Lipopolysaccharide O Antigen of Klebsiella pneumoniae Serotype O1 Is Synthesized by the Product of the rfbDKPO1 Gene* , 1997, The Journal of Biological Chemistry.

[6]  M. McNeil,et al.  Enzymatic synthesis of UDP-galactofuranose and an assay for UDP-galactopyranose mutase based on high-performance liquid chromatography. , 1996, Analytical biochemistry.

[7]  M. McNeil,et al.  Galactofuranose biosynthesis in Escherichia coli K-12: identification and cloning of UDP-galactopyranose mutase , 1996, Journal of bacteriology.

[8]  W. Colli,et al.  Galactofuranose-containing glycoconjugates in trypanosomatids. , 1995, Glycobiology.

[9]  R. Lederkremer,et al.  Synthesis of .alpha.-D-Galactofuranosyl Phosphate , 1994 .

[10]  J. Fischer,et al.  High-Yielding One-Step Conversion of D-Glucose and D-Galactose to the Corresponding α and β Methyl-D-glucofuranosides and Galactofuranosides , 1991 .

[11]  B. Zingales,et al.  Terminal β‐d‐galactofuranosyl epitopes recognized by antibodies that inhibit Trypanosoma cruzi internalization into mammalian cells , 1989 .

[12]  J. Baddiley,et al.  The biosynthesis of galactofuranosyl residues in galactocarolose. , 1971, The Biochemical journal.