Confirmation of the connectivity of 4,8,12,16,20-pentamethylpentacosylphoshoryl beta-D-mannopyranoside, an unusual beta-mannosyl phosphoisoprenoid from Mycobacterium avium, through synthesis.
The synthesis of the title glycolipid is reported. Comparison of the electrospray and high-energy collision-induced dissociation mass spectra of the synthetic material with those reported for the isolate confirm the structure of this unusual antigenic substance with its modified isoprenoid chain.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Dudkin
Vadim
V
D002236:Carbohydrate Conformation; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009162:Mycobacterium avium / Q000737:chemistry; D013237:Stereoisomerism
C458343:4,8,12,16,20-pentamethylpentacosylphoshoryl mannopyranoside; D009005:Monosaccharides; D008358:Mannose