Synthesis of a set of di- and tri-sulfated galabioses.
Among cell-adhesion molecules, L-selectin recognizes sulfated sLe(x) with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLe(x). As a strategy to obtain 3',6',6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4',6'-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield alpha and beta anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3',6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%).
Yoshida
T
T
Department of Microbiology and Immunology, Aichi Medical University, 480-1195, Aichi, Japan. tomo@aichi-med-u.ac.jp
Chiba
T
T
Yokochi
T
T
Onozaki
K
K
Sugiyama
T
T
Nakashima
I
I
D000081:Acetamides; D015815:Cell Adhesion Molecules / Q000737:chemistry / Q000378:metabolism; D062845:Chloroacetates; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D019041:L-Selectin / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D009844:Oligosaccharides / Q000737:chemistry* / Q000378:metabolism; D000080506:Sialyl Lewis X Antigen; D013463:Sulfuric Acid Esters / Q000737:chemistry*; D014238:Trichloroacetic Acid / Q000737:chemistry*
D000081:Acetamides; D015815:Cell Adhesion Molecules; D062845:Chloroacetates; D004187:Disaccharides; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; D013463:Sulfuric Acid Esters; D019041:L-Selectin; C032103:4-O-alpha-D-galactopyranosyl-D-galactose; D014238:Trichloroacetic Acid; C009528:trichloroacetamide