A mild removal of Fmoc group using sodium azide

作者：Chen, Chun Chi; Rajagopal, Basker; Liu, Xuan Yu; Chen, Kuan Lin; Tyan, Yu Chang; Lin, FuI; Lin, Po Chiao^*

来源：Amino Acids, 2014, 46(2): 367-374.

DOI：10.1007/s00726-013-1625-7

• Fluorenylmethoxycarbonyl (Fmoc) deprotection
• Sodium azide
• Solid phase peptide synthesis (SPPS)

A mild method for effectively removing the fluorenylmethoxycarbonyl (Fmoc) group using sodium azide was developed. Without base, sodium azide completely deprotected N (alpha)-Fmoc-amino acids in hours. The solvent-dependent conditions were carefully studied and then optimized by screening different sodium azide amounts and reaction temperatures. A variety of Fmoc-protected amino acids containing residues masked with different protecting groups were efficiently and selectively deprotected by the optimized reaction. Finally, a biologically significant hexapeptide, angiotensin IV, was successfully synthesized by solid phase peptide synthesis using the developed sodium azide method for all Fmoc removals. The base-free condition provides a complement method for Fmoc deprotection in peptide chemistry and modern organic synthesis.

• 出版日期2014-2
• 单位中山大学