Side reactions in the synthesis of phosphotyrosine-containing peptides |
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Authors: | Kalaiyarasi Ramalingam Scott R Eaton Wayne L Cody Joseph A Loo and Annette M Doherty |
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Institution: | (1) Department of Chemistry, Parke-Davis Pharmaceutical Research, Division of the Warner-Lambert Company, 48105 Ann Arbor, MI, U.S.A. |
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Abstract: | Summary A series of phosphopeptides Tyr(PO3H2)-Val-Pro-Xxx-Leu (Xxx=Met, Met(O), Nle, Dab or Cys), derived from the native platelet-derived growth factor- receptor (PDGF-) sequence, has been prepared to study their interaction with the src-homology 2 (SH2) domains of the p85 subunit of PI3 kinase. The phosphopeptides were synthesized using Fmoc methodology incorporating N-Boc dibenzyl-protected phosphotyrosine (Boc-TyrPO3(Bzl)2]) as the N-terminal amino acid, since the benzyl groups can be removed during resin cleavage with TFA. Only peptides containing methionine were found to exist partially as S-benzyl sulfonium salts after TFA cleavage from the resin. The desired peptide could be obtained from the S-benzyl sulfonium salt by hydrogenolysis. |
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Keywords: | N-Boc-Tyr[PO3(Bzl)2]" target="_blank">gif" alt="agr" align="BASELINE" BORDER="0">-Boc-Tyr[PO3(Bzl)2] PDGF-" target="_blank">gif" alt="beta" align="MIDDLE" BORDER="0"> P85 SH2 domains Peptide synthesis Phosphotyrosine S-Benzyl sulfonium salt |
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