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学科主题: 生命有机化学
题名: 1-Ethyl 2-halopyridinium salts, highly efficient coupling reagents for hindered peptide synthesis both in solution and the solid-phase
其他题名: 1-乙基-2-卤吡啶盐:用溶液法或固相法合成有空阻肽的高效缩合剂
作者: Li P(李鹏) ; Xu JC(徐杰诚)
通讯作者: 徐杰诚
刊名: Tetrahedron
发表日期: 2000-01-01
卷: 56, 期:41, 页:8119-8131
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所生命有机国家开放实验室
英文摘要: 1 Ethyl-2-halopyridinium salts, BEP, FEP, BEPH and FEPH, were synthesized and proved to be very effecitive for the synthesis of hindered peptides containing N-methylated of CαCα-dialkylated amino acid residues, HPLC monitoring of model reactions indicated that these pyridinium salts demonstrated higher reactivities, lower racemization than the commonly used halogenated uronium and phosphonium salts. The efficiency of these pyridinium type coupling reagents was further proved by the synthesis of a seres of hindered oligopeptides and active esters with good yields and convenient workup. The 8-11 tetrapeptide fragment of cyclosporin A(CsA) and the pentapeptide moiety of Dolastatin 15 were also successfully synthesized using these pyridinium salts. The efficiency of these pyridinium type coupling reagents for SPPS was also demonstrated by the solid-phase synthesis of the extremely hindered 8-11 peptide segment of CsA and the linear undecapeptide of CsO. The mechanism of the pyridinium salt mediated coupling reactions was also studied by ~1H NMR, IR and HPLC. It was proposed that the major reactive intermediates were the corresponding acyl halide and acyloxypyridinium salts of the N-protected amino acid or peptide.
语种: 英语
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WOS记录号: WOS:000089682200010
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/22622
Appears in Collections:上海有机化学研究所_期刊论文

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Recommended Citation:
Li P,Xu JC. 1-Ethyl 2-halopyridinium salts, highly efficient coupling reagents for hindered peptide synthesis both in solution and the solid-phase[J]. Tetrahedron,2000,56(41):8119-8131.
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