论文总字数：20415字

摘 要

联烯是一类具有丙二烯特殊结构的化合物，由于其特殊结构，所以人们认为其具有热不稳定性，所以虽然此类物质发现的时间比较早，但是人们对其研究不多。直到20世纪，随着大量的具有联烯结构的天然生物分子的发现及其生理以及药理活性，更多的人开始逐渐注意并研究这类化合物。本次我们的工作就是在此类化合物的基础上进行生物偶联反应研究。联烯与半胱氨酸的巯基之间的反应，此反应在水体系中迅速进行，形成一个稳定的、 不可逆的共轭体系，此反应具有优良的选择性和定量转化。酰胺联烯作为新开发的偶联剂，容易与半胱氨酸以及多肽中的自由巯基发生加成反应，该反应条件简单和温和，在生物系统中具有潜在用途。进一步生物研究表明：用荧光标记表明，一个具有末端碳的联烯基团的物质连接上各种不同的分子可能会为对半胱氨酸蛋白的特定标记提供一种新的办法。利用丙二烯类联烯化合物合成相应偶联剂，并与生物有机分子上的特殊官能团进行偶联以达到修饰多肽以及生物蛋白质效果。此次我们使用的生物有机分子是一类常见氨基酸即半胱氨酸，先利用炔烃衍生物合成丙二烯类联烯化合物，最后利用与生物分子上的特定基团偶联，最终向细胞内导入大分子物质，实现其生理及药理活性。该实验研究前景广阔，可以利用其标记功能，在生物医药领域有潜在的应用价值，目前该领域才刚刚取得突破，坚信会有更多的科研人员研究联烯这一类物质。

关键词：联烯 半胱氨酸 末端碳 生物偶联

Biological coupling reaction of allenes based on amide

ABSTRACT

Allene is a kind of compound with special structure of allene, due to its special structure, so people think its thermal instability, so although these substances found time relatively early, but research on it is not much. Until twentieth Century, with the discovery of a large number of natural biological molecules with this structure of the link and its physiological and pharmacological activities, more and more people began to pay attention and study this kind of compounds. Our work is based on the biological coupling reaction of these compounds. The reaction between the allenes and the thiol group of cysteine, which is rapid in the water system, forms a stable and irreversible conjugated system. As a coupling agent of the newly developed, it’s easy to react with the free thiol group of cysteine and polypeptide, which has the advantages of simple and mild reaction conditions, and has potential application in biological system. Further biological studies showed that labeled with fluorescence showed that the terminal carbon of the combined olefinic groups connected to a variety of molecules may provide a new approach for specific markers of protein cysteine. The corresponding coupling agent was synthesized by the use of the combination of propylene and the specific functional groups on the biological organic molecules. The bio organic molecules that we used this time is a kind of common amino acid, first use alkyne derivatives synthesis propylene diene allenic compounds, finally, it is used to couple with the specific group of biological molecules, which will eventually lead to large molecular substances in the cell, and realize their physiological and pharmacological activities. Broad prospects for the experimental study, the marking function have potential application value in the field of biology and medicine. At present, the field has just made a breakthrough, convinced that there will be more and more researchers study this kind of material.

Keywords: Allenes; Cysteine; Cterminal; Biological connectio

目 录

摘 要 I

ABSTRACT II

第一章 文献综述 1

1.1 引言 1

1.2 联烯类化合物的概述 1

1.3 联烯化合物的合成及其加成反应 1

1.3.1 炔烃衍生物合成链端联烯酰胺的反应 3

1.3.2 联烯化合物丙二烯结构的β位加成反应 4

1.3.3 联烯化合物丙二烯结构的β位环加成反应 5

1.4 联烯的偶联反应以及半胱氨酸的化学修饰 5

第二章 联烯化合物的合成及其研究 8

2.1 引言 8

2.2 实验部分 9

2.2.1 实验试剂 9

2.2.2 实验仪器 10

2.2.3 起始原料制备 10

2.2.4 联烯的加成 11

2.3 化合物结构表征： 13

2.4 化合物代表性谱图 14

第三章 结果与讨论 18

第四章 结论与展望 19

参考文献 20

致 谢 24

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