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Design and Synthesis of an Fmoc-SPPS-Compatible Amino Acid Building Block Mimicking the Transition State of Phosphohistidine Phosphatase

2012; American Chemical Society; Volume: 77; Issue: 4 Linguagem: Inglês

10.1021/jo2025702

1520-6904

Martijn F. Eerland, Christian Hedberg,

Mass Spectrometry Techniques and Applications

The synthesis of a sulfonamide-based transition-state (TS) analogue of enzymatic phosphohistidine dephosphorylation as an amino acid building block is presented, together with the proof-of-concept of its incorporation into peptides. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The peptides are designed as inhibitors of phosphohistidine phosphatase and as a pull-down probe for identification of phosphohistidine phosphatases, respectively.