Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 21, Pages 8885-8890Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201599c
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Funding
- NIH, Center for Cancer Research
- NCI-Frederick
- National Cancer Institute, National Institutes of Health
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We had previously reported that Mitsunobu-based introduction of alkyl substituents onto the imidazole N(pi)-position of a key histidine residue in phosphothreonine-containing peptides can impart high binding affinity against the polo-box domain of polo-like kinase 1. Our current paper investigates the mechanism leading to this N(pi)-alkylation and provides synthetic methodologies that permit the facile synthesis of histidine N(pi)-modified peptides. These agents represent new and potentially important tools for biological studies.
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