The methylsulfonylethyloxycarbonyl group, a new and versatile amino protective function.
The methylsulfonylethyloxycarbonyl group, a new and versatile amino protective function.
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甲基磺酰乙氧基羰基，一种新型多功能氨基保护功能。
DOI：
10.1111/j.1399-3011.1975.tb02444.x
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发表时间：
2009
期刊：
影响因子：
--
通讯作者：
I. C. Balvert‐Geers
中科院分区：
文献类型：
--
作者：
G. I. Tesser;I. C. Balvert‐Geers
介绍了一种新的氨基保护基团--甲磺酰乙氧羰基(MSC)，它在多肽合成中与其他常见的基团(苄氧基甲酰基、叔丁氧基甲酰基)结合得很好。它的主要特征是极高的酸稳定性、高的碱稳定性和高极性，提高了它在包括水在内的极性溶剂中的溶解度。该基团可抵抗催化氢解，但不会毒害催化剂。它具有良好的结晶性能。以MSC-Phe-Arg-Trp-Gly-OMe.HCl的合成为例说明了其在多肽合成中的应用。用1.0N的碱(OH-和OCH3-)溶液在5秒内完成对掩蔽四肽的去保护。提出了该基团裂解的反应方案。
A new amino protecting group, the methylsulfonylethyloxycarbonyl (Msc) group, is described which combines well with other familiar groups (benzyloxycarbonyl, t-butyloxycarbonyl) in peptide syntheses. Its main characteristics are an extreme acid stability, a high base lability and a high polarity which enhances solubility in polar solvents including water. The group resists catalytic hydrogenolysis but does not poison the catalyst. It has good crystallizing properties. Application in peptide synthesis is exemplified in the synthesis of Msc-Phe-Arg-Trp-Gly-OMe.HCl. Deprotection of the masked tetrapeptide was accomplished within 5 sec with a 1.0 N solution of base (OH- and OCH3-). A reaction scheme for the cleavage of the group is suggested.