Synthesis of Thiophenylalanine-containing Peptides via Cu(I)-mediated Cross-Coupling
Synthesis of Thiophenylalanine-containing Peptides via Cu(I)-mediated Cross-Coupling
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DOI：
10.1021/ol202947f
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发表时间：
2012-01-20
期刊：
影响因子：
5.2
通讯作者：
Zondlo, Neal J.
中科院分区：
文献类型：
--
作者：
Forbes, Christina R.;Zondlo, Neal J.
芳基硫醇化合物具有独特的反应、氧化还原、电子和光谱性质。通过铜(I)介导的硫代乙酸与含碘苯丙氨酸的多肽在固相中的交叉偶联反应，开发了一种合成含硫苯丙氨酸的多肽的实用方法。这种方法与所有典型的端粒性官能团都是相容的，提供了多肽中芳基硫醇酸盐的一般途径。含有硫代苯丙氨酸(PK(A)6.4)的多肽很容易精制成含有甲基、烯丙基和硝基苄基硫醚、二硫化物、亚硫醚、砜或磺酸盐。
Aryl thiolates have unique reactive, redox, electronic, and spectroscopic properties. A practical approach to synthesize peptides containing thiophenylalanine has been developed via a novel Cu(I)-mediated cross-coupling reaction between thiolacetic acid and iodophenylalanine-containing peptides in the solid phase. This approach is compatible with all canonical protelnogenic functional groups, providing general access to aryl thiolates in peptides. Peptides containing thiophenylalanine (pK(a) 6.4) were readily elaborated to contain methyl, allyl, and nitrobenzyl thioethers, disulfides, sulfoxides, sulfones, or sulfonates.