Carboxybenzyl

Carboxybenzyl

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. [cite journal
title = Über ein allgemeines Verfahren der Peptid-Synthese
author = Max Bergmann, Leonidas Zervas
journal = Berichte der deutschen chemischen Gesellschaft
volume = 65
issue = 7
pages = 1192–1201
year = 1932
url =
doi = 10.1002/cber.19320650722]

References

* J. Clayden, N. Greeves, S. Warren, P. Wothers, "Organic Chemistry", Oxford University Press, 2001


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