Studies on peptides. CLV. Evaluation of trimethylsilyl bromide as a hard-acid deprotecting reagent in peptide synthesis.
Studies on peptides. CLV. Evaluation of trimethylsilyl bromide as a hard-acid deprotecting reagent in peptide synthesis.
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肽的研究。
DOI：
10.1248/cpb.35.3880
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发表时间：
1987
影响因子：
1.7
通讯作者：
H. Yajima
中科院分区：
文献类型：
--
作者：
N. Fujii;A. Otaka;N. Sugiyama;M. Hatano;H. Yajima
在三氟乙酸(TFA)中，三甲基硅基溴(TMSBr)具有裂解苄基保护基团的能力，即苄氧羰基(Z)、苄基(O-BZL)和对甲氧基苄基(S-MBZL)。与目前所研究的其他软亲核试剂相比，添加硫代苯甲醚对反应的加速效果最好。TMSBr/TFA的切割反应速度略慢于三甲基硅基三氟甲磺酸/TFA。而TMSBr/TFA能有效地降低Met(O)，且几乎没有天冬氨酸(Asp)的副反应。将该脱保护方法应用于人胃泌素释放肽的合成。
Trimethylsilyl bromide (TMSBr) in trifluoroacetic acid (TFA) was found to have the ability to cleave benzyl-type protecting groups, i.e., benzyloxycarbonyl (Z), benzyl (O-Bzl) and p-methoxybenzyl (S-MBzl). The reaction was best accelerated by addition of thioanisole, compared with other soft nucleophiles so far examined. The rate of the cleavage reaction with TMSBr/TFA was judged to be somewhat slower than that with trimethylsilyl trifluoromethanesulfonate/TFA. However, TMSBr/TFA reduced Met(O) efficiently and gave almost no side reaction of Asp (succinimide formation). This deprotecting procedure was applied to the synthesis of human gastrin-releasing peptide.