Fmoc-Protein Synthesis: Preparation of Peptide Thioesters Using a Side-Chain Anchoring Strategy |
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Authors: | Pu?Wang Email author" target="_blank">Les?P?MirandaEmail author |
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Institution: | (1) Gryphon Therapeutics, 600 Gateway Blvd, 94080 South San Francisco, CA , USA;(2) Chemistry Research & Discovery, Amgen, Inc, One Amgen Center Drive, MS: 29-M-B Thousand Oaks, CA 91320, USA |
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Abstract: | A side-chain anchoring approach for preparation of peptide thioesters by Fmoc SPPS is reported. This strategy involves the side-chain anchoring of trifunctional amino acids, such as Lys, Glu, Gln, Asp and Asn, for peptide elongation and the post-chain assembly introduction of thioester functionality. This approach allows for the use of standard nucleophilic Fmoc peptide synthesis cycles, which are generally incompatible with thioester-based resin-linkages. The strategy was successfully demonstrated by the straightforward Fmoc syntheses of a model RANTES(1--33) thioester peptide. The Fmoc prepared RANTES(1--33) thioester peptide was then ligated to RANTES(34--68), folded and purified to give the RANTES protein. |
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