• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

酸性α-氨基酸作为酰基供体的应用:芳基酮α-氨基酸及其衍生物的有效立体可控合成。

Utilization of acidic α-amino acids as acyl donors: an effective stereo-controllable synthesis of aryl-keto α-amino acids and their derivatives.

作者信息

Wang Lei, Murai Yuta, Yoshida Takuma, Okamoto Masashi, Tachrim Zetryana Puteri, Hashidoko Yasuyuki, Hashimoto Makoto

机构信息

Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan.

Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University, Kita 21, Nishi 11, Kita-ku, Sapporo 001-0021, Japan.

出版信息

Molecules. 2014 May 16;19(5):6349-67. doi: 10.3390/molecules19056349.

DOI:10.3390/molecules19056349
PMID:24840903
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6271428/
Abstract

Aryl-keto-containing α-amino acids are of great importance in organic chemistry and biochemistry. They are valuable intermediates for the construction of hydroxyl α-amino acids, nonproteinogenic α-amino acids, as well as other biofunctional components. Friedel-Crafts acylation is an effective method to prepare aryl-keto derivatives. In this review, we summarize the preparation of aryl-keto containing α-amino acids by Friedel-Crafts acylation using acidic α-amino acids as acyl-donors and Lewis acids or Brönsted acids as catalysts.

摘要

含芳基酮的α-氨基酸在有机化学和生物化学中具有重要意义。它们是构建羟基α-氨基酸、非蛋白质ogenicα-氨基酸以及其他生物功能成分的有价值中间体。傅克酰基化是制备芳基酮衍生物的有效方法。在本综述中,我们总结了以酸性α-氨基酸为酰基供体,以路易斯酸或布朗斯特酸为催化剂,通过傅克酰基化反应制备含芳基酮的α-氨基酸的方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/1ca0639f32c1/molecules-19-06349-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/95fb0378452e/molecules-19-06349-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/c989b0e43988/molecules-19-06349-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/34b801167607/molecules-19-06349-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/768ac659913c/molecules-19-06349-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/42c5f365bf09/molecules-19-06349-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/23211ba7318a/molecules-19-06349-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/3d510710fc62/molecules-19-06349-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/55c25a8388fe/molecules-19-06349-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/b51dfaf43c31/molecules-19-06349-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/a1d8f9370e9d/molecules-19-06349-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/05c3a8adfa80/molecules-19-06349-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/919b832f5100/molecules-19-06349-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/888be919f371/molecules-19-06349-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/15e34aa6b4ae/molecules-19-06349-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/9b2094958953/molecules-19-06349-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/46c09a432821/molecules-19-06349-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/352c2e4e41ce/molecules-19-06349-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/1ca0639f32c1/molecules-19-06349-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/95fb0378452e/molecules-19-06349-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/c989b0e43988/molecules-19-06349-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/34b801167607/molecules-19-06349-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/768ac659913c/molecules-19-06349-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/42c5f365bf09/molecules-19-06349-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/23211ba7318a/molecules-19-06349-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/3d510710fc62/molecules-19-06349-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/55c25a8388fe/molecules-19-06349-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/b51dfaf43c31/molecules-19-06349-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/a1d8f9370e9d/molecules-19-06349-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/05c3a8adfa80/molecules-19-06349-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/919b832f5100/molecules-19-06349-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/888be919f371/molecules-19-06349-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/15e34aa6b4ae/molecules-19-06349-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/9b2094958953/molecules-19-06349-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/46c09a432821/molecules-19-06349-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/352c2e4e41ce/molecules-19-06349-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/817e/6271428/1ca0639f32c1/molecules-19-06349-g018.jpg

相似文献

1
Utilization of acidic α-amino acids as acyl donors: an effective stereo-controllable synthesis of aryl-keto α-amino acids and their derivatives.酸性α-氨基酸作为酰基供体的应用:芳基酮α-氨基酸及其衍生物的有效立体可控合成。
Molecules. 2014 May 16;19(5):6349-67. doi: 10.3390/molecules19056349.
2
Tunable Aryl Imidazolium Recyclable Ionic Liquid with Dual Brønsted-Lewis Acid as Green Catalyst for Friedel-Crafts Acylation and Thioesterification.可调变芳基咪唑鎓双布朗斯特-路易斯酸可再生离子液体作为绿色催化剂用于傅克酰基化和硫酯化反应。
Molecules. 2020 Jan 15;25(2):352. doi: 10.3390/molecules25020352.
3
Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel-Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester.手性 TFA 保护的 α-氨基芳基-酮衍生物的合成,通过 α-氨基酸 N-羟基琥珀酰亚胺酯的 Friedel-Crafts 酰化反应。
Molecules. 2017 Oct 17;22(10):1748. doi: 10.3390/molecules22101748.
4
Friedel-Crafts Acylation of Aminocarboxylic Acids in Strong Brønsted Acid Promoted by Lewis Base PO.在路易斯碱PO促进下,强布朗斯特酸中氨基羧酸的傅-克酰基化反应
J Org Chem. 2022 Nov 18;87(22):15224-15249. doi: 10.1021/acs.joc.2c01761. Epub 2022 Nov 1.
5
Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel-Crafts acylation/Allan-Robinson reaction.路易斯酸促进通过区域和化学选择性多米诺傅克酰基化/艾伦-罗宾逊反应构建色满-4-酮和异黄酮骨架。
Org Biomol Chem. 2014 Dec 7;12(45):9216-22. doi: 10.1039/c4ob01743a.
6
A protocol for metal triflate catalyzed direct glycosylations with GalNAc 1-OPiv donors.一种使用N-乙酰半乳糖胺1-特戊酰氧基供体进行三氟甲磺酸金属催化直接糖基化反应的方案。
J Org Chem. 2014 Nov 21;79(22):11011-9. doi: 10.1021/jo502036f. Epub 2014 Nov 7.
7
Efficient conversion of triacylglycerols and fatty acids to biodiesel in a microwave reactor using metal triflate catalysts.在微波反应器中使用金属三氟甲磺酸酯催化剂高效转化三酰基甘油和脂肪酸为生物柴油。
Org Biomol Chem. 2010 Oct 21;8(20):4753-6. doi: 10.1039/c0ob00014k. Epub 2010 Aug 17.
8
Protolytic defluorination of trifluoromethyl-substituted arenes.三氟甲基取代芳烃的质子化脱氟反应。
Org Biomol Chem. 2011 Jun 21;9(12):4545-9. doi: 10.1039/c0ob01276a. Epub 2011 May 6.
9
Synthesis of phenol derivatives from cyclohex-2-enones bearing an alkyne through Lewis acid-catalyzed enolization and intramolecular Alder-Rickert reaction.通过路易斯酸催化的烯醇化和分子内 Alder-Rickert 反应,从带有炔烃的环己-2-烯酮合成酚衍生物。
J Org Chem. 2012 Oct 19;77(20):8999-9005. doi: 10.1021/jo301554z. Epub 2012 Oct 4.
10
One-pot protocol to functionalized benzopyrrolizidine catalyzed successively by Rh2(OAc)4 and Cu(OTf)2: a transition metal-Lewis acid catalysis relay.一锅法实现苯并吡咯里西啶的官能团化:由 Rh2(OAc)4 和 Cu(OTf)2 相继催化:一种过渡金属-路易斯酸催化接力。
Org Lett. 2015 Jan 2;17(1):66-9. doi: 10.1021/ol503247t. Epub 2014 Dec 12.

引用本文的文献

1
Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives.新型 4-[(4-氯苯基)磺酰基]苯甲酸衍生物的合成、计算机模拟和体外评估抗菌和毒性特征。
Molecules. 2021 Aug 23;26(16):5107. doi: 10.3390/molecules26165107.
2
Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel-Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester.手性 TFA 保护的 α-氨基芳基-酮衍生物的合成,通过 α-氨基酸 N-羟基琥珀酰亚胺酯的 Friedel-Crafts 酰化反应。
Molecules. 2017 Oct 17;22(10):1748. doi: 10.3390/molecules22101748.

本文引用的文献

1
Hydrogen/deuterium exchange of cross-linkable α-amino acid derivatives in deuterated triflic acid.可交联α-氨基酸衍生物在氘代三氟甲磺酸中的氢/氘交换
Biosci Biotechnol Biochem. 2014;78(7):1129-34. doi: 10.1080/09168451.2014.917267. Epub 2014 Jun 17.
2
Effective Friedel-Crafts acylation of biotin acid chloride in trifluoromethanesulfonic acid.在三氟甲磺酸中生物素酰氯的有效傅克酰基化反应。
Biosci Biotechnol Biochem. 2012;76(11):2162-4. doi: 10.1271/bbb.120553. Epub 2012 Nov 7.
3
Diazirine based photoaffinity labeling.重氮化合物的光亲和标记。
Bioorg Med Chem. 2012 Jan 15;20(2):554-70. doi: 10.1016/j.bmc.2011.06.066. Epub 2011 Jun 29.
4
Novel synthesis of optically active bishomotyrosine derivatives using the Friedel-Crafts reaction in triflic acid.在三氟甲磺酸中利用傅-克反应合成光学活性双高酪氨酸衍生物的新方法。
Biosci Biotechnol Biochem. 2011;75(2):352-4. doi: 10.1271/bbb.100595. Epub 2011 Feb 7.
5
Substituent effects on the reaction of beta-benzoylalanines with Pseudomonas fluorescens kynureninase.取代基对荧光假单胞菌色氨酸酮醇酶与β-苯丙氨酸反应的影响。
Biochemistry. 2010 Sep 14;49(36):7913-9. doi: 10.1021/bi100955b.
6
Effective synthesis of optically active trifluoromethyldiazirinyl homophenylalanine and aroylalanine derivatives with the Friedel-Crafts reaction in triflic acid.在三氟甲磺酸中通过傅克反应有效合成光学活性三氟甲基重氮丙啶基高苯丙氨酸和芳酰基丙氨酸衍生物。
Biosci Biotechnol Biochem. 2009 Jun;73(6):1377-80. doi: 10.1271/bbb.90027. Epub 2009 Jun 7.
7
Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor.作为药物前体的L-高苯丙氨酸的可持续生物催化合成。
Biotechnol Adv. 2009 May-Jun;27(3):286-96. doi: 10.1016/j.biotechadv.2009.01.003. Epub 2009 Jan 22.
8
Homotyrosine-containing cyanopeptolins 880 and 960 and anabaenopeptins 908 and 915 from Planktothrix agardhii CYA 126/8.来自阿氏席藻CYA 126/8的含高酪氨酸的蓝藻肽880和960以及鱼腥藻肽908和915
J Nat Prod. 2009 Jan;72(1):172-6. doi: 10.1021/np800557m.
9
Mild, efficient Friedel-Crafts acylations from carboxylic acids using cyanuric chloride and AlCl3.使用三聚氯氰和三氯化铝从羧酸进行温和、高效的傅克酰基化反应。
Org Lett. 2008 Jul 3;10(13):2645-8. doi: 10.1021/ol800752v. Epub 2008 May 31.
10
Miuraenamides: antimicrobial cyclic depsipeptides isolated from a rare and slightly halophilic myxobacterium.三浦酰胺:从一种稀有且轻度嗜盐的粘细菌中分离出的抗菌环缩肽。
Chem Asian J. 2008 Jan 4;3(1):126-33. doi: 10.1002/asia.200700233.