3-(4-Hydroxymethylphenylsulfanyl)propanoic acid (HMPPA) as a new safety catch linker in solid phase peptide synthesis |
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Authors: | Mikael Erlandsson |
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Affiliation: | Department of Neurochemistry, Stockholm University, 10691 Stockholm, Sweden |
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Abstract: | A new safety catch linker, 3-(4-hydroxymethylphenylsulfanyl)propanoic acid (HMPPA), is described for use in solid phase peptide synthesis. The linker is readily synthesized from commercially available chemicals in a more cost efficient way compared to similar reported linkers. The HMPPA linker is easily attached to an amino derivatized solid support followed by on-resin oxidation of the thioether to sulfoxide, thereby making the linker very stable towards strong acid treatment. Final resin cleavage is performed by reductive acidolysis. |
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Keywords: | AcN, acetonitrile EDT, 1,2-ethanedithiol HMPPA(O), 3-(4-hydroxymethylbenzenesulfanyl)propanoic acid p-ether, petroleum ether TFAA, trifluoroacetic anhydride TFE, trifluoroethanol TMSBr, bromotrimethylsilane |
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