Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles.
Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles.
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DOI：
10.1002/bip.22698
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发表时间：
2015-11
期刊：
影响因子：
2.9
通讯作者：
Burke TR Jr
中科院分区：
文献类型：
--
作者：
Qian WJ;Park JE;Grant R;Lai CC;Kelley JA;Yaffe MB;Lee KS;Burke TR Jr
Our recently discovered, selective, on-resin route to N(τ)-alkylated imidazolium-containing histidine residues affords new strategies for peptide mimetic design. In our current work, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring-forming junctions. Interestingly, these cationic moieties subsequently serve to charge-mask the phosphoamino acid group that directed their formation. Neighbor-directed histidine N(τ)-alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts.
