Neighbor-directed histidine N(τ) alkylation. A route to imidazolium-containing phosphopeptide macrocycles
- National Cancer Inst., Frederick, MD (United States)
- National Cancer Inst., Bethesda, MD (United States)
- Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)
Our recently discovered, selective, on-resin route to N(τ)-alkylated imidazolium-containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring-forming junctions. These cationic moieties subsequently serve to charge-mask the phosphoamino acid group that directed their formation. Furthermore, neighbor-directed histidine N(τ)-alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts.
- Research Organization:
- Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- AC02-06CH11357
- OSTI ID:
- 1228107
- Journal Information:
- Biopolymers, Vol. 104, Issue 6; ISSN 1097-0282
- Country of Publication:
- United States
- Language:
- ENGLISH
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