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首页> 外文期刊>Chemistry: A European journal >Total Synthesis of Mannosyl Tryptophan and Its Derivatives
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Total Synthesis of Mannosyl Tryptophan and Its Derivatives

机译：甘露糖基色氨酸及其衍生物的全合成

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摘要

Glycosylation is one of the most important post- or co-translational modifications of proteins, which affects the biological activities of the parent proteins by influencing the higher-order structure. Recently, a highly novel variant of glycoproteins that incorporate a C-glycosylated amino acid was identified in various proteins. The total synthesis of one such C-glycosyl amino acid, namely, C~2-alpha-D-C-mannosylpyranosyl-L-tryptophan and related peptides were successfully achieved. The mannose and tryptophan moieties were connected via ring opening of benzyl-protected 1,2-anhydro-mannose by a lithiated indole derivative. After the functional group conversion and deprotection steps, the glyco-amino acid was synthesized in a concise and stereoselective manner, in high overall yields. The stereosisomer, C~2-alpha-D-C-glycosylpyranosyl-L-tryptophan was synthesized in a similar way. Furthermore, it was revealed that the inter-mediate azido acid can serve as a useful building block for peptide elongation. A synthetic route for the peptide bond formation of a glycopeptide, without protection of the hydroxyl groups, using the triazine salt derivative as a coupling reagent is also reported.
机译：糖基化是蛋白质最重要的翻译后或共翻译修饰之一，其通过影响高级结构来影响亲本蛋白质的生物学活性。近来，在各种蛋白质中鉴定了结合有C-糖基化氨基酸的糖蛋白的高度新颖的变体。成功实现了一种这样的C-糖基氨基酸，即C〜2-α-D-C-甘露糖基吡喃糖基-L-色氨酸和相关肽的全合成。甘露糖和色氨酸部分通过锂化的吲哚衍生物经由苄基保护的1，2-脱水-甘露糖的开环连接。在官能团转化和脱保护步骤之后，以简洁和立体选择性的方式合成糖氨基酸，具有高的总收率。立体异构体C 2-α-D-C-糖基吡喃糖基-L-色氨酸以类似的方式合成。此外，揭示了中间叠氮基酸可以用作肽延长的有用构建基块。还报道了使用三嗪盐衍生物作为偶联剂在不保护羟基的情况下形成糖肽的肽键的合成途径。

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