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带有叔丁基侧链保护基的Nα-9-芴甲氧羰基氨基酸的制备及其性质

Preparation and properties of Nalpha-9-fluorenylmethyloxycarbonylamino acids bearing tert.-butyl side chain protection.

作者信息

Chang C D, Waki M, Ahmad M, Meienhofer J, Lundell E O, Haug J D

出版信息

Int J Pept Protein Res. 1980 Jan;15(1):59-66. doi: 10.1111/j.1399-3011.1980.tb02550.x.

DOI:10.1111/j.1399-3011.1980.tb02550.x
PMID:7358458
Abstract

The preparation is described by several Nalpha-9-fluorenylmethyloxycarbonylamino acids and derivatives bearing tert.-butyl type side-chain protection of amine, carboxyl, guanido, hydroxyl, imidazol, and sulfhydryl functionalities. Physicochemical properties of these compounds have been determined. Cleavage of the Fmoc group by various amines appears to depend on the base strength and steric hindrance. Premature deblocking of Fmoc group by amine on solid support is very slow and may be negligible under the conditions of solid-phase synthesis.

摘要

该制剂由几种带有叔丁基型胺、羧基、胍基、羟基、咪唑和巯基官能团侧链保护的Nα-9-芴甲氧羰基氨基酸及其衍生物描述。已测定了这些化合物的物理化学性质。各种胺对Fmoc基团的裂解似乎取决于碱强度和空间位阻。胺在固相载体上对Fmoc基团的过早去保护非常缓慢,在固相合成条件下可能可以忽略不计。

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