Development of caged non-hydrolyzable phosphoamino acids and application to photo-control of binding affinity of phosphopeptide mimetic to phosphopeptide-recognizing protein
Development of caged non-hydrolyzable phosphoamino acids and application to photo-control of binding affinity of phosphopeptide mimetic to phosphopeptide-recognizing protein
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DOI：
10.1016/j.bmc.2014.04.002
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发表时间：
2014-06-01
影响因子：
3.5
通讯作者：
Otaka, Akira
中科院分区：
文献类型：
--
作者：
Ebisuno, Koji;Denda, Masaya;Otaka, Akira
描述了笼状的不可水解的磷酸-丝氨酸、-苏氨酸和-酪氨酸衍生物的设计和合成，所述衍生物在UV-照射后产生含有二氟亚甲基单元而不是磷酸酯的氧的母体不可水解的磷酸氨基酸。通过标准Fmoc固相肽合成将笼状不可水解氨基酸掺入肽中，并且通过UV照射将所获得的肽成功地转化为母体不可水解磷酸肽。还报道了笼状的不可水解的含磷酸丝氨酸的肽用于光控制肽与14-3-3 β蛋白的结合亲和力的应用。(C)2014爱思唯尔有限公司版权所有。
The design and synthesis of caged non-hydrolyzable phospho-serine, -threonine, and -tyrosine derivatives that generate parent non-hydrolyzable phosphoamino acids, containing a difluoromethylene unit instead of the oxygen of a phosphoester, after UV-irradiation are described. The caged non-hydrolyzable amino acids were incorporated into peptides by standard Fmoc solid-phase peptide synthesis, and the obtained peptides were successfully converted to the parent non-hydrolyzable phosphopeptides by UV-irradiation. Application of the caged non-hydrolyzable phosphoserine-containing peptide to photo-control the binding affinity of the peptide to 14-3-3 beta protein is also reported. (C) 2014 Elsevier Ltd. All rights reserved.