期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 9, 页码 3583-3586出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo900122c
关键词
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资金
- Natural Sciences and Engineering Research Council (NSERC) of Canada
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-1(43-50)) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.
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