Racemization at Proline Residues during Peptide Bond Formation

  title={Racemization at Proline Residues during Peptide Bond Formation},
  author={Ramakrishnan Nagaraj and Padmanabhan Balaram},
Abdnct-The stepwise synthesis of amino terminal pcntapcptide of alamethiin. Z-Aib-PrpAil+Ala-Aib-OMe, by the dicyclohexylcarbodiimide mediated couplings leads to extensive racemizatiun at the Ala and Pro residues. Racemization is hugely suppressed by the use of additives like N-hydroxysuccinimide and I-hydroxybcnzotriazole. The presence of diastereomeric peptides may be detected by the observation of additional methyl ester and bcnzylic mcthylene signals in the 270 MHz ‘H NMR spectra. Unambiius… CONTINUE READING
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