Fmoc-chemistry of a stable phosphohistidine analogue

We report the synthesis of the phosphohistidine analogue, Fmoc-4-diethylphosphonotriazolylalanine 5 and its incorporation into peptides. Our synthesis of 5 has enabled us to demonstrate that the analogue is compatible with Fmoc-solid phase peptide synthesis (SPPS) conditions. Standard cleavage condi...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (4), p.1297-1299
Hauptverfasser:	McAllister, Tom E, Nix, Michael G, Webb, Michael E
Format:	Artikel
Sprache:	eng
Schlagworte:	Alanine - analogs & derivatives Alanine - chemistry Amino Acid Sequence Analogue Bromides Cleavage Compatibility Fluorenes - chemistry Histidine - analogs & derivatives Histidine - chemistry Peptides Peptides - chemical synthesis Peptides - chemistry Phosphorylation Synthesis
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Beschreibung
Zusammenfassung:	We report the synthesis of the phosphohistidine analogue, Fmoc-4-diethylphosphonotriazolylalanine 5 and its incorporation into peptides. Our synthesis of 5 has enabled us to demonstrate that the analogue is compatible with Fmoc-solid phase peptide synthesis (SPPS) conditions. Standard cleavage conditions yield the diethyl phosphonate-protected peptide, however this can be subsequently deprotected using trimethylsilyl bromide to yield the free phosphonic acid-containing peptides.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/c0cc04238b