Stereoselective synthesis of glycobiosyl phosphatidylinositol, a part structure of the glycosyl-phosphatidylinositol (GPI) anchor of Trypanosoma brucei.
O-alpha-D-Mannopyranosyl-(1-->4)-O-2-amino-2-deoxy-alpha-D-glucopyranosy l- (1-->6)-1D-myo-inositol 1-(1,2-di-O-myristoyl-sn-glycer-3-yl hydrogen phosphate), a part structure of the glycosyl-phosphatidylinositol (GPI) anchor of Trypanosoma brucei, was synthesised efficiently by the phosphonate approach. The glycobiosylinositol core was prepared in a stereocontrolled manner from 1D-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol, tert-butyldimethylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside, and methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-2-thio-alpha-D-mannopyranoside.
Murakata
C
C
RIKEN (The Institute of Physical and Chemical Research), Saitama, Japan.
Ogawa
T
T
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006031:Glycosylation; D017261:Glycosylphosphatidylinositols / Q000138:chemical synthesis* / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D014346:Trypanosoma brucei brucei / Q000737:chemistry*
D017261:Glycosylphosphatidylinositols; C078783:O-mannopyranosyl-1-4-O-2-amino-2-deoxyglucopyranosyl-1-6-myo-inositol 1-(1,2-di-O-myristoyl-sn-glycer-3-yl hydrogen phosphate)