Optimized preparation of deca(L-alanyl)-L-valinamide by 9-fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis on polyethylene glycol-polystyrene (PEG-PS) graft supports, with 1,8-diazobicyclo [5.4.0]-undec-7-ene (DBU) deprotection.
Optimized preparation of deca(L-alanyl)-L-valinamide by 9-fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis on polyethylene glycol-polystyrene (PEG-PS) graft supports, with 1,8-diazobicyclo [5.4.0]-undec-7-ene (DBU) deprotection.
复制标题
DOI：
--
复制
发表时间：
1996-05
期刊：
影响因子：
--
通讯作者：
S. Kates;N. Solé;M. Beyermann;G. Barany;F. Albericio
中科院分区：
文献类型：
--
作者：
S. Kates;N. Solé;M. Beyermann;G. Barany;F. Albericio
十（L-丙氨酰）-L-缬氨酰胺由于其疏水性和形成抑制酰化和脱保护的二级结构的倾向，已知是固相肽合成的具有挑战性的模型靶标。在这里，我们报告了系统的研究，在自动化连续流动仪器上合成这种肽，使用9-芴甲氧羰基（Fmoc）的N α-氨基保护和聚乙二醇聚苯乙烯（PEGPS）接枝支持。结果表明，DBU-哌啶-DMF（1：1：48，vol/vol/vol）是最佳的脱保护剂。合成的肽进行了分析，并通过高效液相色谱和几个质谱技术进行了表征。
Deca(L-alanyl)-L-valinamide is known to be a challenging model target for solidphase peptide synthesis, due to its hydrophobicity and its tendency to form secondary structures which inhibit acylation and deprotection. Here we report systematic studies on the synthesis of this peptide on an automated continuous-flow instrument, using the 9-fluorenylmethyloxycarbonyl (Fmoc) group for N alpha-amino protection and a polyethylene-glycol polystyrene (PEGPS) graft support. The optimal deprotection reagent proved to be DBU-piperidine-DMF (1:1:48, vol/vol/vol). The synthetic peptides were analyzed and characterized by high-performance liquid chromatography and several mass spectrometric techniques.