Access to any site-directed isotopomer of methionine, selenomethionine, cysteine, and selenocysteine - Use of simple, efficient modular synthetic reaction schemes for isotope incorporation
Access to any site-directed isotopomer of methionine, selenomethionine, cysteine, and selenocysteine - Use of simple, efficient modular synthetic reaction schemes for isotope incorporation
复制标题
DOI：
10.1002/ejoc.200400063
复制
发表时间：
2004-06-28
影响因子：
2.8
通讯作者：
Lugtenburg, J
中科院分区：
文献类型：
--
作者：
Siebum, AHG;Woo, WS;Lugtenburg, J
已经制定了允许获得受保护丝氨酸和高丝氨酸的任何同位素的简单模块化反应方案。这些系统可以通过 Mitsunobu 化学简单地转化为半胱氨酸、硒代半胱氨酸、高半胱氨酸、高硒代半胱氨酸、必需氨基酸蛋氨酸和硒代蛋氨酸。这些含硫和硒的氨基酸在生物体中发挥着许多重要作用。此外，高丝氨酸可以通过几个步骤转化为光学活性的L-乙烯基甘氨酸。除了稳定同位素 C-13、N-15、O-17 和 O-18 之外，硫、硒和碳的放射性同位素也可以以定点方式轻松引入。鉴于Mitsunobu反应的广泛范围，我们认为具有丝氨酸和高丝氨酸碳骨架的许多更重要的系统应该可以通过这种基本化学以任何定点同位素标记形式制备。 (C) Wiley-VCH Verlag GmbH & Co. KGaA，69451 魏因海姆，德国，2004 年。
Simple modular reaction schemes that allow access to any isotopomer of protected serine and homoserine have been worked out. These systems could be simply converted into cysteine, selenocysteine, homocysteine, homoselenocysteine, the essential amino acid methionine, and selenomethionine by Mitsunobu chemistry. These sulfur- and selenium-containing amino acids fulfil many essential roles in the living organism. In addition, homoserine could be converted in a few steps into optically active L-vinylglycine. As well as the stable isotopes C-13, N-15, O-17, and O-18, the radioactive isotopes of sulfur, selenium and carbon can also be easily introduced in a site-directed fashion. In view of the wide scope of the Mitsunobu reaction, we feel that many more important systems with the carbon skeleton of serine and homoserine should be preparable through this basic chemistry in any site-directed isotopically labeled form. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.