Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 22, Pages 9954-9958Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo302305d
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Funding
- State of North Rhine-Westphalia (NRW), Germany
- European Union
- 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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