Racemisation of N-Fmoc phenylglycine under mild microwave-SPPS and conventional stepwise SPPS conditions: attempts to develop strategies for overcoming this.

@article{Elsawy2012RacemisationON,
  title={Racemisation of N-Fmoc phenylglycine under mild microwave-SPPS and conventional stepwise SPPS conditions: attempts to develop strategies for overcoming this.},
  author={Mohamed A. Elsawy and Chandralal H Hewage and Brian Walker},
  journal={Journal of peptide science : an official publication of the European Peptide Society},
  year={2012},
  volume={18 5},
  pages={302-11}
}
We have been engaged in the microwave-solid phase peptide synthesis (SPPS) synthesis of the phenylglycine (Phg)-containing pentapeptide H-Ala-Val-Pro-Phg-Tyr-NH(2) (1) previously demonstrated to bind to the so-called BIR3 domain of the anti-apoptotic protein XIAP. Analysis of the target peptide by a combination of RP-HPLC, ESI-MS, and NMR revealed the presence of two diastereoisomers arising out of the racemisation of the Phg residue, with the percentage of the LLLDL component assessed as 49… CONTINUE READING

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