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Base Labile Resins

Both oxime resin and hydroxymethyl benzoic acid linked resin (HMBA resin) can be cleaved with a variety of nucleophilic agents [ammonia or primary amines (amides), hydrazine (hydrazides),methanol/triethylamine (methyl esters),sodium borohydride (alcohols), sodium hydroxide (acids)] to produce the wide range of products indicated from the same precursor resin.  A special application of oxime resin is the formation of cyclic peptides by cyclization cleavage.

Although oxime 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 end-capping should be 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.


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