Sulfur protection with the 3-nitro-2-pyridine sulfenyl group in solid-phase peptide synthesis.
Sulfur protection with the 3-nitro-2-pyridine sulfenyl group in solid-phase peptide synthesis.
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固相肽合成中用 3-硝基-2-吡啶硫基进行硫保护。
DOI：
10.1111/j.1399-3011.1982.tb02634.x
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发表时间：
1982
期刊：
影响因子：
--
通讯作者：
Matsueda,R
中科院分区：
文献类型：
--
作者：
Ridge,RJ;Matsueda,GR;Haber,E;Matsueda,R
在二苯甲胺树脂上分步固相合成Lys 8-加压素（LVP）的过程中，3-硝基-2-吡啶亚硫基（Npys）已成功用于半胱氨酸侧链的保护。通过将该合成与使用3，4-二甲基苄基（DMB）的平行对照合成以及使用两种基团组合的合成进行比较，评价了该组的通用性和局限性。发现Npys基团如所报道的对TFA稳定，并且此外，发现在0°下对HF：苯甲醚（9：1）稳定45分钟，但当硫醇存在于任一试剂中时不稳定。此外，证明了固相肽合成中Npys基团与Boc-苄基合成策略的相容性。通过凝胶过滤和反相HPLC纯化后，获得具有完全生物活性的LVP。
The 3‐nitro‐2‐pyridinesulfenyl(Npys) group has been used successfully for side chain protection of cysteine during the stepwise solid‐phase synthesis of Lys8‐vasopressin(LVP) on benzhydrylamine resin. The versatility and limitations of this group have been evaluated by comparison of this synthesis with a parallel control synthesis using the 3,4‐dimethylbenzyl(DMB) group and with a synthesis utilizing a combination of both groups. The Npys group was found to be stable to TFA as reported and, in addition, was found to be stable to HF:anisole(9:1) for 45 min at 0°, but not when thiol was present in either reagent. Furthermore, compatibility of the Npys group with the Boc‐benzyl synthetic tactic in solid‐phase peptide synthesis was demonstrated. LVP with full biological activity was obtained after purification by gel filtration and reverse‐phase HPLC.