RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1,4-CYCLOHEXADIENE
RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1,4-CYCLOHEXADIENE
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DOI：
10.1021/jo00415a045
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发表时间：
1978-01-01
影响因子：
3.6
通讯作者：
MEIENHOFER, J
中科院分区：
文献类型：
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作者：
FELIX, AM;HEIMER, EP;MEIENHOFER, J
1，4-环己二烯是一种非常有效的氢供体。N-苄氧基羰基、苄酯和苄醚（酪氨酸）保护基可在25 ℃下迅速除去。C与1，4-环己二烯和10% Pd-C催化剂反应。从组氨酸中除去Nim-苄基，从精氨酸中除去Ng-硝基，从丝氨酸和苏氨酸中除去苄基醚基团可以在25 ℃下进行。C使用Pd黑作为催化剂。用1，4-环己二烯催化转移氢化也可从含硫氨基酸上裂解N-苄氧羰基。叔丁基衍生的保护基在这些条件下完全稳定。考察了1，4-环己二烯催化的转移氢化用于去除肽合成中使用的苄基衍生保护基的范围。
1,4-Cyclohexadiene is a very effective H donor for catalytic transfer hydrogenation. N-Benzyloxycarbonyl, benzyl ester, and benzyl ether (tyrosine) protecting groups can be rapidly removed at 25.degree. C with 1,4-cyclohexadiene and 10% Pd-C catalyst. Removal of the Nim-benzyl group from histidine, the Ng-nitro group from arginine, and the benzyl ether groups from serine and threonine can be carried out at 25.degree. C using Pd black as catalyst. Cleavage of N-benzyloxcarbonyl groups from S-containing amino acids was also achieved by catalytic transfer hydrogenation with 1,4-cyclohexadiene. tert-Butyl-derived protecting groups were completely stable under these conditions. The scope of the 1,4-cyclohexadiene-catalyzed transfer hydrogenation for the removal of benzyl-derived protecting groups used in peptide synthesis was examined.