Preparation of the very acid-sensitive Fmoc-Lys(Mtt)-OH. Application in the synthesis of side-chain to side-chain cyclic peptides and oligolysine cores suitable for the solid-phase assembly of MAPs and TASPs.
Preparation of the very acid-sensitive Fmoc-Lys(Mtt)-OH. Application in the synthesis of side-chain to side-chain cyclic peptides and oligolysine cores suitable for the solid-phase assembly of MAPs and TASPs.
复制标题
制备对酸非常敏感的 Fmoc-Lys(Mtt)-OH。
DOI：
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发表时间：
2009
期刊：
影响因子：
--
通讯作者：
P. Mamos
中科院分区：
文献类型：
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作者：
A. Aletras;K. Barlos;D. Gatos;S. Koutsogianni;P. Mamos
N α-9-芴基甲氧羰基-N α-4 =甲基三苯甲基-赖氨酸，[Fmoc-Lys（Mtt）-OH]由赖氨酸经两步制备，总产率为42%。N ε-Mtt官能团可以在用二氯甲烷中的1%TFA或用乙酸/三氟乙醇/二氯甲烷的1：2：7混合物在室温下分别处理30分钟和1小时后定量除去。在这些条件下，叔丁基型基团和肽酯键与TFA-不稳定树脂，如2-氯二苯基甲基-和王-树脂，保持完整。新衍生物在肽合成中的效用已通过环状胆囊收缩素类似物的合成来举例说明。作为进一步应用的一个实例，已经在梅里菲尔德、王和2-氯二苯基甲基树脂上合成了五种类型的赖氨酸核心，其适合于固相合成含有一个、两个或三个表位的抗原肽或模板组装的合成蛋白。
N alpha-9-Fluorenylmethoxycarbonyl-N epsilon-4=methyltrityl-lysine, [Fmoc-Lys(Mtt)-OH], was prepared in two steps from lysine, in 42% overall yield. The N epsilon-Mtt function can be quantitatively removed upon treatment with 1% TFA in dichloromethane or with a 1:2:7 mixture of acetic acid/trifluoroethanol/dichloromethane for 30 min and 1 h at room temperature, respectively. Under these conditions, groups of the tert-butyl type and peptide ester bonds to TFA-labile resins, such as the 2-chlorodiphenylmethyl- and the Wang-resin, remained intact. The utility of the new derivative in peptide synthesis has been exemplified with the synthesis of a cyclic cholecystokinin analog. As an example of further application, five types of lysine cores suitable for the solid-phase synthesis of one, two or three epitopes containing antigenic peptides or template-assembled synthetic proteins have been synthesized on Merrifield, Wang and 2-chlorodiphenylmethyl resin.
胰高血糖素 10-13 区域对其受体相互作用和腺苷酸环化酶激活的重要性。
影响因子：
2.9
作者：
Krstenansky,JL;Trivedi,D;Hruby,VJ
通讯作者：
Hruby,VJ
DOI：
10.1073/pnas.85.15.5409
发表时间：
1988-08-01
影响因子：
11.1
作者：
TAM, JP
通讯作者：
TAM, JP