- omega- concontoxins GVIA和MVIIA二硫化物桥接片段的合成。Npys在Fmoc合成中作为半胱氨酸保护/激活基团的应用。

R G Simmonds, D E Tupper, J R Harris
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引用次数: 0

摘要

3-硝基-2-吡啶磺酸基(Npys)作为半胱氨酸的保护激活基团,特别是在使用Boc策略合成环状和不对称二硫化物的过程中,其效用越来越大。这种化学反应已扩展到通过Fmoc策略组装的肽。通过Boc-Cys(Npys)-OPfp,介绍了n端Cys(Npys)。非n端Cys(Npys)通过与NpysCl发生树脂结合、完全保护的Cys(Acm)肽反应而结合。该方法已被应用于合成四种二硫化物桥接欧米茄- concontoxins GVIA和MVIIA片段。
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Synthesis of disulfide-bridged fragments of omega-conotoxins GVIA and MVIIA. Use of Npys as a protecting/activating group for cysteine in Fmoc syntheses.

The 3-nitro-2-pyridinesulphenyl (Npys) moiety is finding increasing utility as a protecting-activating group for cysteine, particularly in the synthesis of cyclic and unsymmetrical disulfides using the Boc strategy. This chemistry has been extended to peptides assembled by the Fmoc strategy. N-Terminal Cys(Npys) is introduced via Boc-Cys(Npys)-OPfp. Non-N-terminal Cys(Npys) is incorporated by reacting a resin-bound, fully protected Cys(Acm) peptide with NpysCl. This approach has been applied to the synthesis of four disulfide-bridged fragments of omega-conotoxins GVIA and MVIIA.

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