Bergmann-Zervas peptide synthesis

What is Bergmann-Zervas peptide synthesis?

In 1932, Bergmann and Zervas were the first to report on a reaction known as the Bergmann-Zervas peptide synthesis. This process involves converting the amino acid into its N-carbobenzoxy derivative, activating the carboxyl group, forming the peptide with the second amino acid, and then deprotecting it through hydrogenolysis. However, the original method was not suitable for preparing cysteine or cystine peptides, as the catalyst (Pd, Pt) was not active enough in the presence of a molecule containing sulfur.

Bergmann-Zervas peptide synthesis
Bergmann-Zervas peptide synthesis

As a result, the process was modified to include the reductive removal of the carbobenzoxy group by treating the resulting peptide with metallic sodium in liquid ammonia NH3. Over time, other deprotection techniques have been developed, including acidic hydrolysis using phosphonium iodide and hydrogen iodide in acetic acid. Additionally, the carbobenzoxy group can be cleaved using hydrogen bromide HBr or hydrogen chloride HCl.

This method has now become a standard technique for protecting amino groups during peptide synthesis.

References

Bergmann, M. and Zervas, L. (1932), Über ein allgemeines Verfahren der Peptid-Synthese. [On a general method of peptide synthesis.] Ber. dtsch. Chem. Ges. A/B, 65: 1192-1201. https://doi.org/10.1002/cber.19320650722

Shares