Parasite glycoconjugates. Part 16: Synthesis of a disaccharide and phosphorylated di- and tri-saccharides from Leishmania lipophosphoglycan

• Published in: Carbohydrate research Vol. 341; no. 11; pp. 1954 - 1964
• Main Authors: Ross, Andrew J., Sizova, Olga V., Nikolaev, Andrei V.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 14.08.2006; Elsevier
• Subjects: Animals; Biochemistry & Molecular Biology; Carbohydrate Sequence; Carbohydrates; Chemistry; Chemistry, Applied; Chemistry, Organic; Chromatography, Thin Layer; Disaccharides - chemical synthesis; Disaccharides - chemistry; Disaccharides - metabolism; Glycoconjugates - chemical synthesis; Glycoconjugates - chemistry; Glycoconjugates - metabolism; Glycosphingolipids - chemistry; Glycosylation; Glycosyltransferases - metabolism; Leishmania - chemistry; Leishmania donovani - chemistry; Leishmania enzymes; Leishmania major - chemistry; Life Sciences & Biomedicine; Molecular Sequence Data; Molecular Structure; Phosphates; Phosphorylation; Physical Sciences; Science & Technology; Trisaccharides - chemical synthesis; Trisaccharides - chemistry; Trisaccharides - metabolism; Phosphates; Carbohydrates; Glycosylation; Leishmania enzymes; carbohydrates; DONOVANI; glycosylation; MEXICANA; SAND FLY INTERACTIONS; SUBSTRATE-ANALOGS; PHOSPHATE; DEOXY; FRAGMENTS; phosphates; BIOSYNTHESIS; D-MANNOPYRANOSYLPHOSPHATE TRANSFERASE
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2006.03.026

Compounds listed above were synthesised and used for characterisation of novel biosynthetic enzymes (β- d-galactosyl transterases) in Leishmania. A neutral disaccharide β- d-Gal p-(1→4)-α- d-Man p and phosphorylated di- and tri-saccharides β- d-Gal p-(1→3)-[H 2PO 3-6]-β- d-Gal p-O[CH 2] 8CH CH 2 and β- d-Gal p-(1→3)-[H 2PO 3-6]-β- d-Gal p-(1→4)-α- d-Man p, which are fragments of the phosphoglycan portion of the surface lipophosphoglycan from Leishmania donovani (the disaccharide) or Leishmania major (all three compounds), were prepared and used as TLC standards to help the identification and differentiation of the elongating and branching β- d-galactosyl transferase activities in Leishmania. The phosphosaccharides were synthesised using the H-phosphonate method for phosphorylation.