Soluble peptidyl phosphoranes for metal-free, stereoselective ligations in organic and aqueous solution.
Soluble peptidyl phosphoranes for metal-free, stereoselective ligations in organic and aqueous solution.
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DOI：
10.1021/ol202627h
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发表时间：
2012-01
期刊：
影响因子：
5.2
通讯作者：
Ahsanullah;Samer I. Al-Gharabli;J. Rademann
中科院分区：
文献类型：
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作者：
Ahsanullah;Samer I. Al-Gharabli;J. Rademann
介绍了可溶性肽基磷烷的固相合成方法。以Rink酰胺或三烷基膦和三烷基膦与溴乙酰王酯烷基化制备了各种负载型磷酸基酰乙酯。用活化的fmoc氨基酸进行无外消旋的c-酰化，然后进行固相肽合成。酸性条件释放脱羧肽基磷烷到溶液中。该方案允许肽基磷烷的电子变化，研究了在有机和水溶剂中与叠氮化物的连接反应。
Protocols for solid-phase syntheses of soluble peptidyl phosphoranes are presented. Various supported phosphoranylidene acetates were prepared on Rink amide or via alkylation of trialkyl- and triarylphosphines with bromoacetyl Wang ester. C-Acylation was conducted racemization-free with activated Fmoc-amino acids, followed by SPPS (solid-phase peptide synthesis). Acidic conditions released decarboxylated peptidyl phosphoranes into solution. The protocol allowed for the electronic variation of peptidyl phosphoranes which were investigated in ligation reactions with azides in organic and aqueous solvents.