Boc protecting group

from Wikipedia, the free encyclopedia
tert -Butoxycarbonyl-protected glycine . The tert- butoxycarbonyl protective group is marked in blue .

tert -Butyloxycarbonyl (Boc) is a protecting group . Within organic synthesis strategies it prevents the conversion of free amines . The main area of ​​application is the construction of peptides in the context of the classic solid-phase peptide synthesis according to Merrifield .

use

To protect an amine, the Boc group can easily be introduced into a molecule by reacting the amine with di- tert-butyl dicarbonate under a base catalysis :

Introduction of the BOC protective group for an amino acid

The protecting group is stable under many chemical reaction conditions, but is easily attacked by acids. HCl in methanol or trifluoroacetic acid is often used for deprotection. If the Boc group is used in addition to the Fmoc group [(9-fluorenylmethyl) oxycarbonyl-] in a synthesis, the orthogonal protective group strategy is possible: two different amino functions of a molecule can be released in a targeted manner and made to react.

literature