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 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | McAllister, Tom E Nix, Michael G Webb, Michael E |
| description | 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. |
| doi_str_mv | 10.1039/c0cc04238b |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2011-01, Vol.47 (4), p.1297-1299 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | 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 |
| title | Fmoc-chemistry of a stable phosphohistidine analogue |
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