Synthesis and application of N-[1-(4-(4-fluorophenyl)-2,6-dioxocyclohexylidene)ethyl] (Fde)-protected amino acids for optimization of solid-phase peptide synthesis using gel-phase 19F NMR spectroscopy
✍ Scribed by Maciej Pudelko; Weixing Qian; Mikael Elofsson
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 224 KB
- Volume
- 15
- Category
- Article
- ISSN
- 1075-2617
- DOI
- 10.1002/psc.1110
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✦ Synopsis
Abstract
N‐[1‐(4‐(4‐fluorophenyl)‐2,6‐dioxocyclohexylidene)ethyl] (Fde) protected amino acids have been prepared and applied in solid‐phase peptide synthesis monitored by gel‐phase ^19^F NMR spectroscopy. The Fde protective group could be cleaved with 2% hydrazine or 5% hydroxylamine solution in DMF as determined with gel‐phase ^19^F NMR spectroscopy. The dipeptide Ac‐L‐Val‐L‐Val‐NH~2~ 12 was constructed using Fde‐L‐Val‐OH and no noticeable racemization took place during the amino acid coupling with N,N′‐diisopropylcarbodiimide and 1‐hydroxy‐7‐azabenzotriazole or Fde deblocking. To extend the scope of Fde protection, the hydrophobic nonapeptide LLLLTVLTV from the signal sequence of mucin MUC1 was successfully prepared using Fde‐L‐Leu‐OH at diagnostic positions. Copyright © 2009 European Peptide Society and John Wiley & Sons, Ltd.