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化学进展 2020, Vol. 32 Issue (1): 55-71 DOI: 10.7536/PC190505 前一篇   后一篇

所属专题： 电化学有机合成

• •

脱氢氨基酸的合成及其在药物研发中的应用

王童, 文姣, 李良春, 郑仁林, 孙德群*()   

  1. 1. 西南科技大学生命科学与工程学院 绵阳 621000
  • 收稿日期:2019-05-08 出版日期:2020-01-15 发布日期:2019-12-11
  • 通讯作者: 孙德群
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Synthesis of Dehydroamino Acids and Their Applications in the Drug Research and Development

Tong Wang, Wenjiao Zhao, Liangchun Li, Renlin Zheng, Dequn Sun*()   

  1. 1. School of Life Science and Engineering, Southwest University of Science and Technology, Mianyang 621000, China
  • Received:2019-05-08 Online:2020-01-15 Published:2019-12-11
  • Contact: Dequn Sun
  • About author:
    *E-mail:

传统多肽所具有的容易被酶解、细胞膜通透性差以及构象容易发生变化等缺点,限制了它作为药物在疾病治疗领域的应用。将脱氢氨基酸引入多肽,对其进行构象限制,能够有效改善它的代谢稳定性和生物利用度。本文主要综述了α,β-脱氢-α-氨基酸、β,γ-脱氢-α-氨基酸、α-脱氢-β-氨基酸、α,β-脱氢-β-氨基酸四种脱氢氨基酸的合成方法以及近几年来在药物设计中的应用,希望为相关的研究提供参考。

关键词： 脱氢氨基酸, 模拟肽, 构象限制, 合成, 药物设计

Traditional polypeptides usually have the disadvantages of easy hydrolyzation, poor cell membrane permeability, and unstable conformation, which limits their application as a drug in the field of disease treatment. The conformational restriction caused by incorporation of dehydroamino acids into polypeptide can effectively improve the metabolic stability and bioavailability of peptides. In this paper, the synthesis methods and the recent applications in drug design of four kinds of dehydroamino acids including α,β-dehydro-α-amino acids, β,γ-dehydro-α-amino acids, α-dehydro-β-amino acids and α,β-dehydro-β-amino acids are reviewed, which could provide reference for the related research.

Key words: dehydroamino acids, peptidomimetics, conformational restriction, synthesis, drug design
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图式1 α,β-脱氢-α-氨基酸的Z、E异构体[11]
Scheme. 1 The Z, E isomers of α,β-dehydro-α-amino acids[11]
图式2 β,γ-脱氢-α-氨基酸Z、E异构体[30]
Scheme. 2 The Z, E isomers of β,γ-dehydro-α-amino acids[30]
表1 MTT法检测的四种N保护的α,β-脱氢丙氨酸衍生物在三株肿瘤细胞和非肿瘤细胞(MRC-5)中的IC50(μM)值[32]
Table 1 IC50 (μM)values of the N-protected α,β-dehydroalanine derivatives assessed in A549, AGS, SH-SY5Y and MRC-5 cell lines by MTT assay[32]
α,β-Dehydroalanine
derivatives		 A549 AGS SH-SY5Y MRC-5
5 > 62.5 29.4 23.9 > 62.5
6 > 62.5 60.3 62.3 > 62.5
7 > 62.5 36.8 21.0 > 62.5
8 > 62.5 54.6 42.4 > 62.5
图式3 四种α,β-脱氢丙氨酸衍生物化学结构[32]
Scheme. 3 Chemical structure of four α,β-dehydroalanine derivatives[32]
图式4 ΔFd的化学结构[33]
Scheme. 4 Chemical structure of ΔFd[33]
图式5 甲维激素和艾维激素的化学结构[41,42]
Scheme. 5 Chemical structures of methoxyvinylglycine and aminoethoxyvinylglycine[41,42]
图式6 β-羟基消除法合成α,β-脱氢-α-氨基酸[43,44]
Scheme. 6 Synthesis of α,β-dehydro-α-amino acids by β-hydroxyl elimination[43,44]
图式7 Phomopsin A和B的化学结构[45]
Scheme. 7 Chemical structure of phomopsin A and B[45]
图式8 两种脱氢苯丙氨酸类似物[46]
Scheme. 8 Two dehydrophenylalanine analogues[46]
图式9 3-邻苯二甲酰-1,5-苯并二氮杂卓-2-酮衍生物的合成路线[47]
Scheme. 9 The synthesis route of 3-phthalimido-1,5-benzodiazepine-2-one derivatives[47]
图式10 N-取代消除法合成α,β-脱氢-α-氨基酸[52]
Scheme. 10 Synthesis of α,β-dehydro-α-amino acids by N-hydroxyl/chlorinated elimination[52]
图式11 HWE反应合成α,β-脱氢-α-氨基酸[54,55]
Scheme. 11 Synthesis of α,β-dehydro-α-amino acids by HWE reaction[54,55]
图式12 NOSO-95C的化学结构[56]
Scheme. 12 The chemical structure of NOSO-95[56]
图式13 Telcagepant的化学结构[57]
Scheme. 13 The chemical structure of Telcagepant[57]
图式14 Erlenmeyer合成法及口恶唑酮开环合成α,β-脱氢-α-氨基酸[59]
Scheme. 14 Synthesis of α,β-dehydro-α-amino acids by erlenmeyer synthesis and oxazolone ring opening[59]
图式15 Topuzyan合成的具有抗胆碱酯酶活性的化合物[61]
Scheme. 15 Synthesis of compound with anticholinesterase activity by Topuzyan [61]
图式16 由硝基化合物合成α,β-脱氢-α-氨基酸[62]
Scheme. 16 Synthesis of α,β-dehydro-α-amino acids by nitro compound[62]
图式17 雅库酰胺A的化学结构[66]
Scheme. 17 The chemical structure of Yaku’amide A[66]
图式18 铜催化交叉偶联合成α,β-脱氢-α-氨基酸[66]
Scheme. 18 Synthesis of α,β-dehydro-α-amino acids by Cu-catalyzed cross-coupling method[66]
图式19 炔酯亲核加成合成α,β-脱氢-α-氨基酸[67]
Scheme. 19 Synthesis of α,β-dehydro-α-amino acids by nucleophilic addition of alkynyl ester[67]
图式20 环二肽2,5-二酮哌嗪的化学结构[69]
Scheme. 20 The chemical structure of cyclodipeptide 2,5-diketopiperazines[69]
图式21 Schöllkopf反应合成α,β-脱氢-α-氨基酸[71]
Scheme. 21 Synthesis of α,β-dehydro-α-amino acids by Schöllkopf reaction[71]
图式22 化合物56~59的化学结构[73]
Scheme. 22 The chemical structures of compounds 56~59[73]
图式23 由α-酮酸酯合成α,β-脱氢-α-氨基酸[76]
Scheme. 23 Synthesis of α,β-dehydro-α-amino acids by α-keto acids ester[76]
图式24 Antrimycins的化学结构[76]
Scheme. 24 The chemical structure of Antrimycins[76]
图式25 由MAHOs合成α,β-脱氢-α-氨基酸[79]
Scheme. 25 Synthesis of α,β-dehydro-α-amino acids by MAHOs[79]
图式26 由α,β-不饱和酯合成α,β-脱氢-α-氨基酸[81]
Scheme. 26 Synthesis of α,β-dehydro-α-amino acids by α,β-unsaturated ester[81]
图式27 炭疽致死性因子抑制剂的化学结构[83]
Scheme. 27 The chemical structure of AnthraxLethal factor inhibitor[83]
图式28 通过Mukaiyama-Michael加成反应合成α,β-脱氢-α-氨基酸[84]
Scheme. 28 Synthesis of α,β-dehydro-α-amino acids by Mukaiyama-Michael addition[84]
图式29 四种环状α,β-脱氢-α-氨基酸 [86]
Scheme. 29 Four cyclic α,β-dehydro-amino acids[86]
图式30 Li的环状脱氢氨基酸合成路线[87]
Scheme. 30 Li’s synthetic route of cyclic α,β-dehydro-amino acids[87]
图式31 Kublitskii的环状脱氢氨基酸合成路线[88]
Scheme. 31 Kublitskii’s synthetic route of cyclic α,β-dehydro-amino acids[88]
图式32 Huy的环状脱氢氨基酸合成路线[89]
Scheme. 32 Huy’s synthetic route of cyclic α,β-dehydro-amino acids[89]
图式33 Williams的环状脱氢氨基酸合成路线[90]
Scheme. 33 Williams’ synthetic route of cyclic α,β-dehydro-amino acids[90]
图式34 Palacios的环状脱氢氨基酸合成路线[91]
Scheme. 34 Palacios’ synthetic route of cyclic α,β-dehydro-amino acids[91]
图式35 由α-烯基酸加成反应合成β,γ-脱氢-α-氨基酸[21,94,95]
Scheme. 35 Synthesis of β,γ-dehydro-α-amino acids by α-alkenyl acids[21,94,95]
图式36 由α-氨基酸氧化后热解合成β,γ-脱氢-α-氨基酸[97,100,101]
Scheme. 36 Synthesis of β,γ-dehydro-α-amino acids by oxidation and pyrolysis of α-amino acids[97,100,101]
图式37 缩醛法合成β,γ-脱氢-α-氨基酸[102, 103]
Scheme. 37 Synthesis of β,γ-dehydro-α-amino acids by acetal method[102,103]
图式38 口恶唑烷开环合成β,γ-脱氢-α-氨基酸[105]
Scheme. 38 Synthesis of β,γ-dehydro-α-amino acids by oxazolane open-loop[105]
图式39 (S,Z)-APPA的合成路线[108]
Scheme. 39 Synthetic route of (S,Z)-APPA[108]
图式40 双环原甲酸酯保护法合成β,γ-脱氢-α-氨基酸[109]
Scheme. 40 Synthesis of β,γ-dehydro-α-amino acids by cyclic ortho ester protection[109]
图式41 高丝氨酸内酯开环合成β,γ-脱氢-α-氨基酸[111]
Scheme. 41 Synthesis of β,γ-dehydro-α-amino acids by ring opening of high-serine lactone[111]
图式42 环状β,γ-脱氢-α-氨基酸的合成[113,114,115]
Scheme. 42 Synthesis of cyclic β,γ-dehydro-α-amino acids[113,114,115]
图式43 三种β-脱氢氨基酸的化学结构
Scheme. 43 The chemical structure of three β-dehydroamino acids
图式44 Rajesh的α-脱氢-β-氨基酸合成路线[117]
Scheme. 44 Rajesh’s synthetic route of cyclic α-dehydro-β-amino acids[117]
图式45 Paira的α-脱氢-β-氨基酸合成路线[120]
Scheme. 45 Paira’s synthetic route of α-dehydro-β-amino acids[120]
图式46 Ghosh的α-脱氢-β-氨基酸合成路线[121]
Scheme. 46 Ghosh’s synthetic route of α-dehydro-β-amino acids[121]
图式47 Buchholz 和Hoffmann的α-脱氢-β-氨基酸合成路线[123]
Scheme. 47 The α-dehydro-β-amino acids synthetic route of Buchholz and Hoffmann[123]
图式48 Tanaka合成的糜蛋白酶抑制物[125]
Scheme. 48 The chymotrypsin inhibitor synthesized by Tanaka[125]
图式49 Bierbaum的α-脱氢-β-氨基酸合成路线[127]
Scheme. 49 The α-dehydro-β-amino acids synthetic route of Bierbaum[127]
图式50 通过aza-Morita-Baylis-Hillman反应合成α-脱氢-β-氨基酸[128]
Scheme. 50 Synthesis of α-dehydro-β-amino acids by aza-Morita-Baylis-Hillman reaction[128]
图式51 Crotanecine的化学结构[130]
Scheme. 51 The chemical structure of Crotanecine[130]
图式52 Reeve的α,β-脱氢-β-氨基酸合成路线[131]
Scheme. 52 The α,β-dehydro-β-amino acids synthetic route of Reeve[131]
图式53 Jeong的α,β-脱氢-β-氨基酸合成路线[132]
Scheme. 53 The α,β-dehydro-β-amino acids synthetic route of Jeong[132]
图式54 Liu的α,β-脱氢-β-氨基酸合成路线[134]
Scheme. 54 The α,β-dehydro-β-amino acids synthetic route of Liu[134]
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