Kessler Martin, Glatthar Ralf, Giese Bernd, Bochet Christian G
Department of Chemistry, University of Basel, 19 St. Johanns-Ring, CH-4056 Basel, Switzerland.
Org Lett. 2003 Apr 17;5(8):1179-81. doi: 10.1021/ol027454g.
[reaction: see text] A sequential solid-phase peptide synthesis was developed using both photolabile linker and protecting groups. The chromatic sequential lability between a tert-butyl ketone-derived linker (sensitive to irradiation at 305 nm) and a nitroveratryloxycarbonyl (NVOC) group (sensitive at 360 nm) was exploited to prepare Leu-Enkephalin in a 55% overall yield. This new strategy allows the preparation of peptides in essentially neutral medium, by avoiding the use of common deprotection reagents such as trifluoroacetic acid or piperidine.
[反应：见正文] 开发了一种使用光不稳定连接基和保护基的连续固相肽合成方法。利用叔丁基酮衍生连接基（对305nm辐射敏感）和硝基藜芦氧基羰基（NVOC）基团（对360nm敏感）之间的颜色顺序不稳定性，以55%的总收率制备亮氨酸脑啡肽。这种新策略通过避免使用常见的脱保护试剂（如三氟乙酸或哌啶），能够在基本中性的介质中制备肽。
