4.7 Article

Silyl-Based Alkyne-Modifying Linker for the Preparation of C-Terminal Acetylene-Derivatized Protected Peptides

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JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 22, 页码 9954-9958

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AMER CHEMICAL SOC
DOI: 10.1021/jo302305d

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  1. State of North Rhine-Westphalia (NRW), Germany
  2. European Union
  3. European Regional Development Fund

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A novel linker for the synthesis of C-terminal acetylene-functionalized protected peptides is described. This SAM1 linker is applied in the manual Fmoc-based solid-phase peptide synthesis of Leu-enkephalin and in microwave-assisted automated synthesis of Maculatin 2.1, an antibacterial peptide that contains 18 amino acid residues. For the cleavage, treatment with tetramethylammonium fluoride results in protected acetylene-derivatized peptides. Alternatively, a one-pot cleavage-click procedure affords the protected 1,2,3-triazole conjugate in high yields after purification.

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