Acid‐labile anchoring linkages for solid phase synthesis of C‐terminal asparagine peptides using the Fmoc strategy
- 1 August 1990
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 36 (2) , 182-187
- https://doi.org/10.1111/j.1399-3011.1990.tb00964.x
Abstract
Two acid‐labile substituted benzylamine type anchoring linkages, 4‐benzoxy‐2,6‐dimethoxybenzylamine and 2‐benzoxy‐4,6‐dimethoxybenzylamine, for solid phase synthesis of peptide amides were prepared. The Na‐9‐fluorenylmethyloxycarbonyl (Fmoc) amino acids could be easily attached to the resins with DCC/HOBt (loading 0.5–0.6 mmol/g resin). After final removal of the Na‐protecting groups, treatment with TFA (50–95%) yielded amino acid and peptide amides in high purity. As we could show for the synthesis of thymulin (FTS, pGlu‐Ala‐Lys‐Ser‐Gln‐Gly‐Gly‐Ser‐Asn), these two resins with anchoring linkages are well suited for the synthesis of C‐terminal Asn peptides using protected aspartic acid derivative as starting material.Keywords
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