Sodium-liquid ammonia reduction in peptide chemistry
Sodium-liquid ammonia reduction in peptide chemistry
复制标题
肽化学中的钠液氨还原
DOI：
10.1021/cr00061a004
复制
发表时间：
1984
期刊：
影响因子：
62.1
通讯作者：
I. Schőn
中科院分区：
文献类型：
--
作者：
I. Schőn
引入钠液氨还原以去除苄基型和甲苯磺酰基保护基团是大约 50 年前肽化学史上的一个重要里程碑1-3，并对其快速发展做出了重大贡献，导致 1935 年合成了肌肽 2，1936 年合成了谷胱甘肽 4，1954 年合成了催产素^ 9，1954 年合成了赖氨酸 10-13 和1957 年，精氨酸-va-sopressins14-17 被提出。三十多年来，这种方法在含有半胱氨酸残基的肽的合成中是不可或缺的。 1955 年诺贝尔化学奖获得者文森特·杜维尼奥 (Vincent du Vigneaud) 在这项工作中做出了不可磨灭的贡献。尽管对不良副反应的认识引起了人们对其应用局限性的关注，但钠液氨还原仍然是合成催产素18和加压素19类似物的成熟方案，并且最近在由31个氨基酸残基组成的人/3-内啡肽合成的最后一步中强调了其相对于氟化氢酸解的优势。 20 尽管许多优秀的教科书21-28从不同的角度论述了钠液氨还原在一般有机和肽化学领域中的应用的某些方面，但迄今为止尚未发表对此主题的全面综述。本综述的范围包括肽化学中钠-液氨还原去除保护基的结果，特别强调副反应。包括在其他领域获得的一些数据，例如碳水化合物、核苷酸、杂环化学等。最近的发现29-31可能会给钠的应用带来新的推动力
The introduction of sodium-liquid ammonia reduc-tion for the removal of benzyl-type and tosyl protecting groups was an essential milestone in thehistory of peptide chemistry about 50 years ago1-3 and significantly contributed to its speedy development resulting in the synthesis of carnosine2 in 1935, glutathione4 in 1936, oxytocin^ 9 in 1954, lysine-10-13 and arginine-va-sopressins14-17 in 1957. Over three decades this method was indispensable in the synthesis of peptides con-taining cysteine residues. Vincent du Vigneaud, the Nobel Prize Laureate of 1955 in chemistry, rendered an imperishable service in this work. Though the recognition of undesiredside reactions drew attention to the limits of itsapplications, the so-dium-liquid ammonia reduction is still a well-established protocol for the synthesis of analogues of oxy-tocin18 and the vasopressins, 19 and its advantages over acidolysis with hydrogen fluoride were recently em-phasized in the laststep of the synthesis of human/3-endorphin consisting of 31 amino acid residues. 20 Although a number of excellent textbooks21-28 deal from different points of view with some aspects of the application of sodium-liquid ammonia reduction in the field of general organic and peptide chemistry, no comprehensive review on this topic has been hitherto published. The scope of this review comprises the re-sults of sodium-liquid ammonia reduction in the re-moval of protecting groups in peptide chemistry with special emphasis on side reactions. Some data obtained in other fields, eg, carbohydrate, nucleotide, heterocyclic chemistry, etc., are included. Recent findings29-31 may give a new impetus to the application of sodium-