Handbook on Syntheses of Amino Acids: General Routes for the Syntheses of Amino Acids
Handbook on Syntheses of Amino Acids: General Routes for the Syntheses of Amino Acids
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氨基酸合成手册：氨基酸合成的一般路线
DOI：
10.1021/ja1097622
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发表时间：
2010
期刊：
影响因子：
--
通讯作者：
D. Berkowitz
中科院分区：
文献类型：
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作者：
D. Berkowitz
在这篇论文中，布拉斯科维奇阐述了“在过去的150年里”氨基酸化学的最重要的发展。这是一项相当艰巨的任务，显然需要行使一些编辑许可来削减这一点，以便这样的报道可能会被集中在一本专著中，尽管篇幅很大。这一领域的经典著作是威廉姆斯的《光学活性R-氨基酸合成》(Pergamon，1989)，虽然这本书的结构和写作非常好，但它现在已经有20年的历史了，因此需要补充。虽然这本手册不是威廉姆斯的书的替代品，但这本手册基本上涵盖了大约2006年的文献，从而填补了两卷之间的很大一部分空白。在主题上，布拉斯科维奇寻求涵盖更广泛的合成空间，并将其中相当大一部分用于外消旋氨基酸的合成。正如他指出的那样，在某些情况下，拆分外消旋体可能比进行立体选择性合成更实用和/或经济。事实上，这可能是过程化学家有用的参考，因为它的重点是氨基酸，特别是那些必须大规模生产和富含对映体的氨基酸。作者还对拆分、色谱分离和立体分析方法进行了广泛的讨论。第一章写得很好，对这一领域进行了令人满意的概述，从20种传统蛋白质产生氨基酸的基础知识，到“第21和第22种氨基酸”、L-硒半胱氨酸和L-吡咯赖氨酸等令人着迷的最新发现。作者讨论了一些天然和非天然氨基酸的药物化学，甚至还探讨了神经活性氨基酸的现代生物学和生物化学，如D-丝氨酸。通过这种方式，他成功地传达了该领域的兴奋之情，该领域包括合成、药物和生物化学的重要方面。在组织方面，目录做得很巧妙，极大地帮助读者浏览这部密集的作品。但这些指数就不能这么说了。尽管这项工作在感觉和风格上与马奇的高级有机化学相似，但它将从马奇使用的多种指数中受益匪浅。Blaskovich确实提供了一个相当好的关键字索引，但没有针对作者或转换的索引，这可能是3月出版的书在许多版本中最有用的编目功能。这位读者强烈建议作者在以后的任何版本中将这些特性添加到本书中。毫不奇怪，这本书中更具概念创新的化学大部分是从20世纪70年代和80年代初与Schöllkopf等人讨论不对称氨基酸合成的“黄金时代”开始的，以及
In this treatise, Blaskovich sets out to cover the most important developments in amino acid chemistry “in the last 150 years.” This is a rather daunting task, and clearly some editorial license needed to be exercised to pare this down so that such coverage might be captured in one, albeit voluminous, monograph. The classic work in this area is Synthesis of Optically ActiVe R-Amino Acids (Pergamon, 1989) by Williams, and although this book was exceptionally well constructed and written, it is now two decades old and, thus, in need of a supplement.Although not a replacement for Williams’s book, this handbook basically covers the literature through about 2006 and, thereby, fills a significant portion of the gap between the two volumes. Thematically, Blaskovich seeks to cover broader synthetic space and dedicates a significant amount of it to the synthesis of racemic amino acids. As he points out, it may be more practical and/or economical, in some cases, to resolve the racemate rather than engage in stereoselective synthesis. Indeed, this will likely be a useful reference for the process chemist, given its focus on amino acids, particularly those that must be produced on large scale and in enantio-enriched form. The author also provides extensive discussion of resolution, chromatographic separation, and stereoanalytical methods. Chapter 1 is well written and provides a satisfying overview of the field, from the basics of the 20 traditional proteinogenic amino acids to the fascinating, more recent discoveries of the “21st and 22nd amino acids”, L-selenocysteine and L-pyrrolysine. The author discusses some of the medicinal chemistry of natural and unnatural amino acids and even ventures into the modern biology and biochemistry of neuroactive amino acids, such as D-serine. In this way, he successfully conveys the excitement of the field, which encompasses important aspects of synthetic, medicinal, and biological chemistry. In terms of organization, the Table of Contents is masterfully done and helps the reader enormously to navigate this dense work. The same cannot be said for the indices. Although this work is similar in feel and style to March’s AdVanced Organic Chemistry, it would have benefited greatly from the sort of multiple indices that March employed. Blaskovich does provide a reasonably good keyword index, but there are no indices for either authors or transformations, which is perhaps the most useful cataloguing feature of the March book in its many editions. This reader strongly encourages the author to add these features to this volume in any future editions. Not surprisingly, the bulk of the conceptually more innovative chemistry featured in this book begins with a discussion of the “golden days” of asymmetric amino acid synthesis with the likes of Schöllkopf in the 1970s and early 1980s and the major