【摘要】：α,β-二氨基酸是許多天然產(chǎn)物的結(jié)構(gòu)單元,是生物活性化合物的關(guān)鍵結(jié)構(gòu)片段,它及其衍生物多應(yīng)用于醫(yī)藥和生物化學(xué)方向。近些年來,它的作用越來越突出。α,β-二氨基酸及其衍生物的合成方法現(xiàn)已發(fā)展了不少。但是,大多合成步驟冗長,反應(yīng)條件苛刻。因此,尋找更高效合成α,β-二氨基酸及其衍生物的方法有重要意義。在生物體內(nèi),含有自由氨基的化合物可以直接參與反應(yīng),例如,酶催化的甘氨酸可以對親電試劑(如醛)的直接加成生成β-羧基α-氨基酸,該反應(yīng)條件溫和,甘氨酸直接參與反應(yīng),不需要任何保護(hù)基。酶作為催化劑,它的活性中心是維生素B6,其包括吡哆醇、吡哆醛及吡哆胺。受此啟發(fā),我們設(shè)想如果將親電試劑由醛換成亞胺,用吡哆醛衍生物作為催化劑有可能實(shí)現(xiàn)甘氨酸酯對亞胺的加成,得到一系列α,β-二氨基酸衍生物,并且得到一定的非對映選擇性。該論文的研究工作包括:(1)設(shè)計(jì)并合成一系列的維生素B6衍生物(吡哆醛衍生物),并用以探索催化合成α,β-二氨基酸衍生物反應(yīng)的可行性;(2)篩選出催化效果最好的吡哆醛化合物,并優(yōu)化反應(yīng)條件,主要是對溶劑、堿的當(dāng)量比、堿的種類、反應(yīng)物當(dāng)量比、溫度和底物濃度進(jìn)行優(yōu)化;(3)在最優(yōu)條件下對該反應(yīng)物進(jìn)行一定的底物拓展。
[Abstract]:偽, 尾 -diamino acids are the structural units of many natural products, and they are the key structural fragments of bioactive compounds. They and their derivatives are widely used in medicine and biochemistry. In recent years, its function is more and more prominent. The synthesis of 偽, 尾 -diamino acid and its derivatives has been developed a lot. However, most of the synthesis steps are lengthy and the reaction conditions are harsh. Therefore, it is of great significance to find a more efficient method for the synthesis of 偽, 尾-diamino acids and their derivatives. In organisms, compounds containing free amino groups can be directly involved in the reaction. For example, enzymatic glycine can directly add to electrophilic reagents such as aldehydes to form 尾 -carboxyl 偽 -amino acids under mild conditions. Glycine is directly involved in the reaction and does not require any protective groups. The active center of the enzyme is vitamin B 6, which includes pyridoxine, pyridoxal and pyridoxamine. Inspired by this, we assume that if the electrophilic reagent is changed from aldehydes to imines and pyridoxal derivatives are used as catalysts, the addition of glycine esters to imines can be realized, and a series of 偽, 尾 -diamino acid derivatives can be obtained. And a certain enantioselectivity was obtained. The research work in this paper includes: (1) designing and synthesizing a series of vitamin B6 derivatives (pyridoxal derivatives) and exploring the feasibility of catalytic synthesis of 偽, 尾 -diamino acid derivatives; (2) screening out the most effective pyridoxal compounds. The reaction conditions were optimized, such as solvent, alkali equivalent ratio, alkali type, reactant equivalent ratio, temperature and substrate concentration. (3) the substrate was expanded under the optimal conditions.
【學(xué)位授予單位】：上海師范大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2016
【分類號】：O621.251

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