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Side reactions in the synthesis of phosphotyrosine-containing peptides

✍ Scribed by Kalaiyarasi Ramalingam; Scott R. Eaton; Wayne L. Cody; Joseph A. Loo; Annette M. Doherty

Publisher
Springer Netherlands
Year
1994
Tongue
English
Weight
390 KB
Volume
1
Category
Article
ISSN
1573-3149

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✦ Synopsis

A series of phosphopeptides Tyr(POsH2)-Val-Pro-Xxx-Leu (Xxx = Met, Met(O), Nle, Dab or Cys), derived from the native platelet-derived growth factor-J3 receptor (PDGF-I3) 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-Tyr[PO3(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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