Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl beta-D-arabinofuranosyl phosphates.
Described is the synthesis of polyprenyl 2-deoxy-2-fluoro-beta-D-arabinofuranosyl phosphate derivatives, including an analog of decaprenyl beta-D-arabinofuranosyl phosphate, the donor species used by the arabinosyltransferases involved in mycobacterial cell-wall biosynthesis. The targets were synthesized via a route involving the synthesis of a protected beta-D-arabinofuranosyl phosphate derivative, its coupling with a polyprenyl trichloroacetimidate, and then deprotection of the resulting product. The use of arabinofuranosyl phosphates with the monosaccharide hydroxyl groups protected as either silyl ethers or benzoate esters was explored. Although the coupling yields between the phosphate and polyprenyl trichloroacetimidates were comparable with either type of protecting group, access to the benzoyl-protected derivative was more efficient and therefore gave the products in higher overall yield.
Joe
Maju
M
Department of Chemistry and Alberta Ingenuity Centre for Carbohydrate Science, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Canada AB T6G 2G2.
Lowary
Todd L
TL
D001089:Arabinose / Q000031:analogs & derivatives / Q000138:chemical synthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D010428:Pentosephosphates / Q000138:chemical synthesis*; D011105:Polyisoprenyl Phosphate Sugars / Q000138:chemical synthesis*; D013729:Terpenes / Q000138:chemical synthesis
D010428:Pentosephosphates; D011105:Polyisoprenyl Phosphate Sugars; D013729:Terpenes; C089328:decaprenyl-P-arabinose; C028055:arabinose 5-phosphate; D001089:Arabinose