Silver trifluoromethanesulphonate as an S-deprotecting reagent for the synthesis of cystine peptides

Silver trifluoromethanesulphonate as an S-deprotecting reagent for the synthesis of cystine peptides
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DOI:
10.1039/c39890000283
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发表时间:
1989
期刊:
Journal of The Chemical Society, Chemical Communications
影响因子:
--
通讯作者:
N. Fujii;A. Otaka;Toshihiro Watanabe;A. Okamachi;H. Tamamura;H. Yajima;Y. Inagaki;M. Nomizu;K. Asano
N. Fujii;A. Otaka;Toshihiro Watanabe;A. Okamachi;H. Tamamura;H. Yajima;Y. Inagaki;M. Nomizu;K. Asano
中科院分区:
其他
文献类型:
--
作者:
N. Fujii;A. Otaka;Toshihiro Watanabe;A. Okamachi;H. Tamamura;H. Yajima;Y. Inagaki;M. Nomizu;K. Asano

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乙酰氨基甲基(Acm)基团连接在巯基功能的半胱氨酸被发现被切割定量的处理与银三氟甲磺酸在三氟乙酸,这种试剂是更有效的比银三氟乙酸和切割的S-苯甲酰氨基甲基和S-对甲氧基苄基以及,这种新的S-脱保护剂已被用于催产素和鸡降钙素的合成。
The acetamidomethyl (Acm) group attached at the thiol function of cysteine was found to be cleaved quantitatively by treatment with silver trifluoromethanesulphonate in trifluoroacetic acid, this reagent being more effective than silver trifluoroacetate and cleaved the S-benzamidomethyl and the S-p-methoxybenzyl groups as well; this new S-deprotecting reagent has been used in the synthesis of oxytocin and chicken calcitonin.