Synthesis of photolabile mono- and di-valent α-d-mannoside-6-phosphates as chemically modifying probes for mannose-6-phosphate-receptors

✍ Scribed by Jochen Lehmann; Frank Schweizer; Uwe P. Weitzel

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 570 KB
• Volume: 273
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)91131-6

✦ Synopsis

Two photoaffinity probes, disodium 3'-azibutyl t~-D-mannopyranoside-6-phosphate and tetrasodium 2-azi-l,10-bis(a-D-mannopyranosyloxy-6-phosphate)decane were synthesized for the regioselective chemical modification of mannose-6-phosphate receptors. Disodium 3'-azibutyi t~-Dmannopyranoside-6-phosphate was obtained by chemical a-mannosylation of 3-azibutanol and subsequent 6-phosphorylation of the mannosyl residue. The corresponding divalent ligand, mimicking a high mannose oligosaccharide with two mannose-6-phosphate end groups, was obtained by the same procedure but with 2-azi-l,10-decanediol as the aglyconic alcohol. In preliminary experiments, both photolabile ligands had affinity to cation-independent mannose-6phosphate receptors from bovine testes.