炔酰胺类缩合剂研究进展

doi:10.6023/cjoc202011022

有机化学 ›› 2021, Vol. 41 ›› Issue (3): 873-887.DOI: 10.6023/cjoc202011022 上一篇下一篇

所属专题：热点论文虚拟合集

研究专题

炔酰胺类缩合剂研究进展

刘涛^a^,^b, 许泗林^c, 赵军锋^a^,^b^,^*()

a 西北工业大学化学制造研究院西安 710072
b 江西师范大学化学化工学院南昌 330022
c 许昌学院数理学院河南许昌 461000

收稿日期:2020-11-16 修回日期:2020-12-11 发布日期:2020-12-24
通讯作者: 赵军锋

作者简介:

刘涛, 2017年毕业于江西农业大学理学院, 2018年进入江西师范大学化学化工学院有机化学专业攻读硕士学位, 师从赵军锋教授. 主要从事多肽绿色合成方法研究.

许泗林, 2015年于许昌学院获得学士学位, 2015~2020年在江西师范大学赵军锋教授课题组硕博连读, 于2020年7月获得博士学位, 同年9月进入许昌学院任讲师. 主要研究方向为多肽的化学合成与修饰和新型荧光探针的设计与合成.

赵军锋, 教授, 洪堡学者. 2001年和2005年分别于北京师范大学和华中师范大学获学士和硕士学位. 2010年获新加坡南洋理工大学博士学位. 2010~2013年先后于南洋理工大学、德国波恩大学和明斯特大学从事化学生物学方向学的博士后研究; 2013~2014年任香港大学化学系助理教授(研究); 2014~2020年任江西师范大学教授、博士生导师; 2021年起,任西北工业大学教授、博士生导师. 课题组致力于通过发展有机化学新反应和新试剂来解决化学生物学的前沿科学问题, 研究兴趣集中在多肽与蛋白质的化学合成与精准修饰及其化学生物学研究.

基金资助:
国家自然科学基金(21778025); 国家自然科学基金(91853114)

Recent Advances in Ynamide Coupling Reagent

Tao Liu^a^,^b, Silin Xu^c, Junfeng Zhao^a^,^b^,^*()

a Institute of Advanced Synthesis, Northwestern Polytechnical University, Xi'an 710072
b College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
c School of Science, Xuchang University, Xuchang, Henan 461000

Received:2020-11-16 Revised:2020-12-11 Published:2020-12-24
Contact: Junfeng Zhao
About author:
* Corresponding author. E-mail: zhaojf@jxnu.edu.cn
Supported by:
National Natural Science Foundation of China(21778025); National Natural Science Foundation of China(91853114)

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摘要/Abstract

缩合剂是指用于促成羧酸与胺或者醇直接缩合构建酰胺键或酯键的一类试剂的总称. 由于酰胺和酯的重要性, 缩合剂的开发成为了学术界与工业界广泛关注的一个重要研究方向. 多肽合成就是α-氨基酸在缩合剂的作用下反复形成酰胺键的过程, 因此, 缩合剂在多肽合成中发挥着至关重要的作用. 当前多肽合成所使用的试剂和技术大多是20世纪50~80年代发展起来的, 这些试剂和技术的天生弊端逐渐显现出来. 比如传统多肽缩合剂过度活化α-氨基酸而诱发的外消旋化和其它副反应导致的副产物成为药物多肽生产过程中一个极为关切的问题. 另外固相多肽合成的低原子经济性给可持续发展带来了极大的挑战. 这些问题只能依靠原始创新的颠覆性技术和全新的缩合方法来解决. 我们课题组致力于通过发展新试剂和新反应来解决多肽与蛋白质化学合成领域的难题. 本文系统介绍了我们发展的一种结构全新的炔酰胺类缩合试剂及其在酰胺、酯、大环内酯、多肽、硫代多肽合成中的应用研究进展.

关键词: 炔酰胺, 缩合剂, 酰胺键, 多肽合成, 酯键, 大环内酯, 硫代多肽

Coupling or condensation reagents are compounds that can be used to promote the direct condensation of carboxylic acids with amines or alcohols to furnish amide or ester bond, respectively. Since their discovery, coupling reagents have been widely used in the manufacture of drugs, materials, cosmetics and other fine chemicals containing amide or ester bond. In particular, coupling reagent plays a crucial role in the chemical synthesis of peptides which involves the iterative amide bond formation between proteinogenic α-amino acids. However, current peptide synthesis methods and strategies are mainly relied on the reagents and techniques developed in 1950~1980s, and are reaching a high standard and their inherent limits. For example, the impurities and racemization/epmimerization caused by over activation of conventional coupling reagents have become major concerns of peptide drug manufacture. Moreover, the poor atom economy of the solid phase peptide synthesis results in large amount of chemical waste, and thus posing formidable challenge to the sustainable development. Only disruptive innovations involving new reagents and novel condensation mechanism can solve the notorious issues that plague current peptide synthesis. In this context, our research group disclosed that ynamide could be used as a novel coupling reagent to promote amide and ester bond formation via the condensation of carboxylic acids with amines or alcohols. More importantly, ynamide coupling reagents could also be used for peptide bond formation in a racemization free manner. Herein, the discovery as well as the application of ynamide coupling reagent in the construction of amide and ester bonds is systematically summarized.

Key words: ynamide, coupling reagent, amide bond, peptide synthesis, ester bond, macrolactone, thiopeptide

引用此文

刘涛, 许泗林, 赵军锋. 炔酰胺类缩合剂研究进展[J]. 有机化学, 2021, 41(3): 873-887.

Tao Liu, Silin Xu, Junfeng Zhao. Recent Advances in Ynamide Coupling Reagent[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 873-887.

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图/表 22

图式1. 羧酸与胺缩合构建酰胺键

Scheme 1. Amide bond formation from condensation of carboxylic acid and amine

图式2. 多肽合成过程中消旋的反应机理

Scheme 2. Racemization mechanism during peptide bond formation

图1. 代表性消旋抑制剂

Figure 1. Representative racemization suppressors

图2. 代表性缩合剂

Figure 2. Representative coupling reagents

图式3. 炔烃类缩合剂介导的酰胺键形成

Scheme 3. Alkyne coupling reagents mediated amide bond formation

图式4. 炔酰胺类缩合剂的发现

Scheme 4. Discovery of ynamide coupling reagents

图式5. 炔酰胺介导的“一锅法”合成酰胺

Scheme 5. Ynamide-mediated “one-pot” synthesis of aimdes

表1. 炔酰胺的构效关系a

Table 1. Optimization of the ynamide

表2. 炔酰胺介导的酰胺合成a

Table 2. Ynamide-mediated amide synthesis

Entry	Coupling reagent	Additive	Time	Yield^b/%	dr^c
1	HBTU	DIEA	10 min	90	82∶18
2	HATU	DIEA	10 min	70	87∶13
3	PyBop	DIEA	10 min	91	88∶12
4	DEPBT	DIEA	20 min	61	99∶1
5	DCC	—	10 min	98	91∶9
6	MYMsA	—	22 h	99	>99∶1
7	MYTsA	—	22 h	94	>99∶1

表3. 各类缩合剂在多肽合成过程中外消旋化程度的研究对比a

Table 3. Comparative study of racemization/epimerization of peptide bond formation

表4. 炔酰胺介导的多肽合成a

Table 4. Ynamide-mediated peptide synthesis

图式6. 炔酰胺介导的分子间酯化反应及大环内酯化反应

Scheme 6. Ynamide-mediated intermolecular esterification and macrolactonization

表5. 炔酰胺介导的分子间酯化反应a

Table 5. Ynamide-mediated intermolecular esterification

表6. 炔酰胺介导的大环内酯化反应a

Table 6. Ynamide-mediated macrolactonization

Entry	Reaction conditions	I I:II'^b	Yield^c/%	dr
1	DCC, DMAP, CSA, CHCl₃, r.t., 4 h	98∶2	34	89∶11
2	EDCI, HOAT, DMAP, CH- Cl₃, r.t., 4 h	69∶31	13	37∶63
3	HBTU, DMAP, CHCl₃, r.t., 2 h	90∶10	20	23∶77
4	TBTU, HOAT, DMAP, CH₂- Cl₂, r.t., 1 h	>99∶1	33	69∶31
5	HATU, DMAP, CHCl₃, r.t., 30 min	78∶22	38	93∶7
6	PyBop, DMAP, CH₂Cl₂, r.t., 2 h	46∶54	12	27∶73
7	PySSPy, PPh₃, MeCN, 80 ℃, 8 h	21∶79	5	92∶8
8	PPh₃, DEAD, THF, r.t., 48 h	>99∶1	6	29∶71
9	2-methyl-6-nitrobenzoic anhydride, DMAP, NEt₃, toluene, 25 ℃	nd	(52)	94∶6
10	MYTsA, PTSA?H₂O, CH₂- Cl₂, r.t., 10 min	>99∶1	87 (92)	>99∶1

表7. 大环内酯化方法对比a

Table 7. Comparative study of macrolactonization methods

图式7. 炔酰胺介导的硫代酰胺合成

Scheme 7. Ynamide-mediated thioamide synthesis

表8. 选择性地合成硫酰化试剂a

Table 8. Chemoselective synthesis of thioacylation reagents

表9. 炔酰胺介导的硫代多肽合成a

Table 9. Ynamide-mediated thioamide substituted peptide synthesis

图式8. 硫代脑啡肽的合成

Scheme 8. Synthesis of trithioamide-substituted Leu-enkephalin

图式9. 通过固相合成在多肽主链骨架上精准引入硫代酰胺键修饰

Scheme 9. Site-specific incorporation of thioamide substitution into a peptide backbone via solid phase peptide synthesis

表10. 炔酰胺介导的硫羰基酯和二硫酯的合成a

Table 10. Ynamide-mediated thionoester and dithioester synthesis

表11. 一锅法合成炔酰胺a

Table 11. A robust one-step approach to ynamides

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炔酰胺类缩合剂研究进展

Recent Advances in Ynamide Coupling Reagent

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