Protecting-group-based colorimetric monitoring of fluorous-phase and solid-phase synthesis of oligoglucosamines.
A new hydroxyl protecting group, nitrophthalimidobutyric (NPB) acid, has been synthesized in one solvent-free step for colorimetric monitoring of reaction cycles upon its facile removal with hydrazine acetate in the solid-phase and fluorous-phase syntheses of antigenic oligoglucosamines associated with infectious Staphylococcus aureus. The NPB group serves as a convenient hydroxyl protecting group that is stable to the basic conditions required for the synthesis of the common trichloroacetimidate protecting groups, the strongly acidic conditions used in glycosylation reactions, as well as conditions commonly used to remove silicon-based protecting groups.
Ko
Kwang-Seuk
KS
Department of Chemistry and the Plant Sciences Institute, Gilman Hall, Iowa State University, Ames, Iowa 50011-3111, USA.
Park
Gisun
G
Yu
Yang
Y
Pohl
Nicola L
NL
D000941:Antigens / Q000737:chemistry; D003124:Colorimetry; D005944:Glucosamine / Q000737:chemistry*; D006878:Hydroxides / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry*; D013203:Staphylococcal Infections; D013211:Staphylococcus aureus
D000941:Antigens; D006878:Hydroxides; D011108:Polymers; C031356:hydroxide ion; D005944:Glucosamine