Oxime Resin

Oxime Resin
Oxime resin is a synthesis resin compatible with Boc chemistry. Peptides can be cleaved from
this resin under basic conditions which leave the side chain and N-terminal protecting groups in
place, making this resin very useful for preparing protected peptide fragments that can be used in
the segment condensation synthesis of larger peptides.
This resin is also useful for preparing structural analogs which differ only at the C-terminal. By
using different alkyl amines to displace the peptide from the resin, a series of N-alkylamides of the
same peptide can be prepared. Likewise, using DBU and different alcohols a variety of peptide
esters can be prepared. Using acetate salts of amino acid esters produces a series of peptide
analogs that differs only in the C-terminal amino acid.
Although this resin is compatible with Boc chemistry, the oxime ester linkage is susceptible to
TFA. Therefore the Boc group is removed with 25% TFA in DCM during synthesis and endcapping is performed after each coupling to block any active sites on the resin that may have
been exposed. For best results, the peptide should not exceed 10 residues.