Improved synthesis of phytanylƒnƒÑ-D-cellobiosyldiphosphate as substrate for ƒÑ-D-mannosyltransferase

BARRIOS P.; IELPI L.; MARINO C.

ARKIVOC - ONLINE JOURNAL OF ORGANIC CHEMISTRY

ARKAT USA INC

Lugar: new Jersey; Año: 2011 vol. 2011 p. 38 - 48

1551-7004

Polyisoprenyl-pyrophosphate-linked cellobiose is the natural acceptor of the a-1,3-mannosyltransferase AceA from Acetobacter xylinum, which transfers mannose from GDP-mannose during the assembly of the heptasaccharide repeat unit of the exopolysaccharide acetan. Phytanyl  a-D-cellobiosyldiphosphate (4) has been previously synthesized as an analogue acceptor by condensation of hepta-O-acetyl-a-D-cellobiosylphosphate (1) with phytanylphosphate (2), but the procedure was briefly described. We report here a modified detailed synthesis of 4. The complete NMR characterization of 4 is provided and also a selection of NMR signals of all the intermediate compounds which facilitate monitoring the synthesis.