The trichloroethyl (TCE) group is shown to be a viable protecting group for sulfonates. TCE-protected sulfonates were found to be particularly stable to acid, a key characteristic that led to a straightforward enantioselective synthesis of L-FmocPhe(p-CH2SO3TCE)OH. This was used as a building block for the solid phase synthesis of an octapeptide corresponding to P-selectin glycoprotein ligand-1 residues 43-50 (PSGL-143-50) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.
قسم البحث
مجلة البحث
Journal of Organic Chemistry
الناشر
NULL
تصنيف البحث
1
عدد البحث
74
موقع البحث
DOI: 10.1021/jo900122c
سنة البحث
2009
المشارك في البحث
ملخص البحث