Carboxybenzyl

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Schematic: Protection of amine with benzyl chloroformate
Schematic: Protection of amine with benzyl chloroformate

Carboxybenzyl or Cbz or Z is an amine protecting group in organic synthesis. It is commonly used in peptide synthesis and is formed by reacting an amine with benzyl chloroformate and a weak base. It is used to protect amines from electrophiles. The protected amine can be deprotected by catalytic hydrogenation or treatment with HBr.

The method was first used by Max Bergmann in 1932 for the synthesis of peptides.[1]

[edit] References

  1. ^ Max Bergmann, Leonidas Zervas (1932). "Über ein allgemeines Verfahren der Peptid-Synthese". Berichte der deutschen chemischen Gesellschaft 65 (7): 1192–1201. doi:10.1002/cber.19320650722. 
  • J. Clayden, N. Greeves, S. Warren, P. Wothers, "Organic Chemistry", Oxford University Press, 2001
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