Trichloroethyl Group As a Protecting Group for Sulfonates and Its Application to the Synthesis of a Disulfonate Analog of the Tyrosine Sulfated PSGL-143-50 Peptide
Trichloroethyl Group As a Protecting Group for Sulfonates and Its Application to the Synthesis of a Disulfonate Analog of the Tyrosine Sulfated PSGL-143-50 Peptide
复制标题
DOI：
10.1021/jo900122c
复制
发表时间：
2009-05-01
影响因子：
3.6
通讯作者：
Taylor, Scott D.
中科院分区：
文献类型：
--
作者：
Ali, Ahmed M.;Hill, Bryan;Taylor, Scott D.
三氯乙基（TCE）基团被证明是一个可行的保护基磺酸盐。发现TCE保护的磺酸盐对酸特别稳定，这是导致直接对映选择性合成L-FmocPhe（p-CH 2SO 3 TCE）OH的关键特征。将其用作固相合成对应于P-选择素糖蛋白配体-1残基43-50（PSGL-1（43-50））的八肽的结构单元，其中磺基酪氨酸残基46和48被（磺基甲基）苯丙氨酸（SmP）（一种重要的水解稳定的磺基酪氨酸模拟物）取代。
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.