Identification and Suppression of beta-Elimination Byproducts Arising from the Use of Fmoc-Ser(PO(3)Bzl,H)-OH in Peptide Synthesis
Troy J Attard, Neil M O'Brien-Simpson, Eric C Reynolds
INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS | SPRINGER | Published : 2009
The formation of 3-(1-piperidinyl)alanyl-containing peptides via phosphoryl β-elimination was identified from the application of Fmoc-Ser(PO 3Bzl,H)-OH in peptide synthesis as shown by RP-HPLC, ES-MS and 31P-NMR analysis. An N α -deprotection study using the model substrates, Fmoc-Xxx(PO3Bzl,H)-Val-Glu(O tBu)-Resin (Xxx = Ser, Thr or Tyr) demonstrated that piperidine-mediated phosphoryl β-elimination occurred in the N-terminal Ser(PO3Bzl,H) residue at a ratio of 7% to the target phosphopeptide, and that this side reaction did not occur in the corresponding Thr(PO 3Bzl,H)- or Tyr(PO3Bzl,H)- residues. The generation of 3-(1-piperidinyl)alanyl-peptides was also shown to be enhanced by the use o..View full abstract
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Awarded by National Health and Medical Research Council
This work was supported by the National Health and Medical Research Council grant 454475 and The CRC for Oral Health Science. We would like to thank Dr. Chris Barlow for the provision of the FT-ICR mass spectral data.