The Preparation of Peptides Using Mixed Carbonic—Carboxylic Acid Anhydrides
The Preparation of Peptides Using Mixed Carbonic—Carboxylic Acid Anhydrides
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混合碳酸-羧酸酐制备肽
DOI：
10.1021/ja01123a028
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发表时间：
1952
影响因子：
15
通讯作者：
Ruth L. Osato
中科院分区：
文献类型：
--
作者：
J. R. Vaughan;Ruth L. Osato
N-取代的氨基酸或肽与烷基碳酸的混合酸酐在无水条件下在低温下形成，并使其与氨基酸或肽酯或与氨基酸盐反应，得到高产率的相应肽或更高级的肽。所用烷基碳酸的选择并不重要，并且反应不会因形成不利的副产物而复杂化。确定了反应的最佳条件，并应用于一系列肽酯的制备。用这种方法没有观察到光学活性物质的外消旋化。在我们对混合酸酐作为酰化剂用于合成肽的研究的继续中，我们对N-取代氨基酸和烷基碳酸的混合酸酐的行为进行了研究。这些酸酐或酰基烷基碳酸酯特别令人感兴趣，因为理论上它们提供的优点是，在任何主要形成酰胺的反应中，形成的唯一副产物将是二氧化碳和由所用烷基碳酸衍生的醇;即
Mixed anhydrides of N-substituted aminoacids or peptides with alkylcarbonic acids are formed at low temperature under anhydrous conditions and allowed to react with aminoacid or peptide esters or with aminoacid salts to give good yields of the corresponding peptides or higher peptides. Choice of the alkylcarbonic acid used is not critical and the reaction is not complicated by the formation of unfavorable by-products. The optimum conditions for the reaction havebeen determined and applied in the preparation of a series of peptides esters. No racemization of optically-active materials hasbeen observed by this method.In a continuation of our investigations on the use of mixed anhydrides as acylating agents for the synthesis of peptides, 1 an examination was made of the behavior of mixed anhydrides of N-substituted aminoacids and alkylcarbonic acids. These anhydrides, or acylalkylcarbonates, were of particular interest since theoretically they offered the advantage that, in any predominantly amide-forming reaction, the only by-products formed would be carbondioxide and an alcohol derived from the alkylcarbonic acid used; ie