English
新闻公告
More
化学进展 2018, Vol. 30 Issue (6): 737-752 DOI: 10.7536/PC171110 前一篇   后一篇

• 综述 •

基于天然小分子化合物的超分子手性自组装

高玉霞1,2, 梁云1, 胡君3*, 巨勇1*   

  1. 1. 清华大学化学系 生命有机磷化学及化学生物学教育部重点实验室 北京 100084;
    2. 中国农业大学理学院 北京 100094;
    3. 北京化工大学 软物质科学与工程高精尖创新中心 北京 100029
  • 收稿日期:2017-11-13 修回日期:2018-01-05 出版日期:2018-06-15 发布日期:2018-03-07
  • 通讯作者: 胡君,e-mail:jhu@mail.buct.edu.cn;巨勇,e-mail:juyong@tsinghua.edu.cn E-mail:jhu@mail.buct.edu.cn;juyong@tsinghua.edu.cn
  • 基金资助:
    国家自然科学基金项目(No.21472108,21604085,21772112)、国家重点研发计划(No.2017YFD0200302)和吉林省青年科研基金项目(No.20160520135JH)资助

Supramolecular Chiral Self-Assembly Based on Small Molecular Natural Products

Yuxia Gao1,2, Yun Liang1, Jun Hu3*, Yong Ju1*   

  1. 1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China;
    2. College of Science, China Agricultural University, Beijing 100094, China;
    3. Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China
  • Received:2017-11-13 Revised:2018-01-05 Online:2018-06-15 Published:2018-03-07
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No.21472108,21604085,21772112),the National Key R&D Program of China (No.2017YFD0200302),and the Jilin Science Foundation for Youths (No.20160520135JH).
超分子手性普遍存在于自然界和生命体内,可通过分子在非共价键作用下有序排列形成,对生命科学、药物化学及材料科学的发展起着重要的作用。天然产物来源广泛,具有独特的立体结构和多手性中心,由于其分子手性可以在组装过程中随着分子的有序堆积得到传递和放大,形成超分子手性结构,因此是一类优良的超分子手性构筑基元。研究天然产物的手性自组装,不仅可以拓展其在超分子化学中的应用,还能深化人们对自然界和生命体中手性现象的理解。本文总结了近年来甾体、三萜、氨基酸、糖等天然产物小分子化合物在超分子手性自组装方面的研究进展及其未来的发展前景。
Supramolecular chirality, one of the most fascinating phenomena in nature and life, can be generated from orderly molecular self-assembly under non-covalent interactions, and plays an important role in life science, pharmaceutical chemistry, and materials science. Natural products, which are abundant in nature, have attracted immense attention in supramolecular chirality due to their unique stereostructures and multiple chiral centers. By transferring and magnifying the molecular chirality into supramolecular assemblies, natural products have been regarded as one of the ideal building blocks in fabricating supramolecular chiral nanostructures. The study of chiral assembly behavior of natural products will not only expand their applications in supramolecular chemistry, but also help us better understand the chiral phenomena in nature and life. In this review, recent developments of supramolecular chiral self-assembly based on small molecular natural products, such as steroids, triterpenoids, amino acids, sugars, and so on, are summarized and their prospects are discussed.
Contents
1 Introduction
2 Chiral self-assembly based on small molecular natural products
2.1 Chiral self-assembly of steroids
2.2 Chiral self-assembly of triterpenoids
2.3 Chiral self-assembly of amino acids
2.4 Chiral self-assembly of sugars
2.5 Chiral self-assembly of other natural products
3 Conclusion

中图分类号: 

()
[1] Smith D K. Chem. Soc. Rev., 2009, 38:684.
[2] Crassous J. Chem. Soc. Rev., 2009, 38:830.
[3] 袁菁(Yuan J), 张莉(Zhang L), 黄昕(Huang X), 姜思光(Jiang S G), 刘鸣华(Liu M H). 化学进展(Progress in Chemistry), 2005, 17(5):780.
[4] Duan P F, Cao H, Zhang L, Liu M H. Soft Matter, 2014, 10:5428.
[5] 莽朝永(Mang C Y), 赵霞(Zhao X), 刘彩萍(Liu C P), 吴克琛(Wu K C). 化学学报(Acta Chimica Sinica), 2008, 66(2):195.
[6] 靳清贤(Jin Q X), 李晶(Li J), 李孝刚(Li X G), 张莉(Zhang L), 方少明(Fang S M), 刘鸣华(Liu M H). 化学进展(Progress in Chemistry), 2014, 26(6):919.
[7] Paik P, Gedanken A, Mastai Y. ACS Appl. Mater. Inter., 2009, 1:1834.
[8] Cao H, Zhu X F, Liu M H. Angew. Chem. Int. Ed., 2013, 52:4122.
[9] 徐括喜(Xu K X), 刘顺英(Liu S Y), 何永炳(He Y B), 秦海娟(Qin H J), 卿光焱(Qing G Y), 胡翎(Hu L). 化学学报(Acta Chimica Sinica), 2006, 64(21):2205.
[10] Liu C X, Jin Q X, Lv K, Zhang L, Liu M H. Chem. Commun., 2014, 50:3702.
[11] Miao W G, Yang D, Liu M H. Chem. Eur. J., 2015, 21:7562.
[12] Stepanenko V, Li X Q, Gershberg J, Würthner, F. Chem. Eur. J., 2013, 19:4176.
[13] George S J, Tomovi? ?, Schenning A P H J, Meijer E W. Chem. Commun., 2011, 47:3451.
[14] George S J, Tomovi? ?, Smulders M M J, de Greef T F A, Leclère P E L G, Meijer E W, Schenning A P H J. Angew. Chem. Int. Ed., 2007, 46:8206.
[15] Shen Z C, Wang T Y, Liu M H. Angew. Chem. Int. Ed., 2014, 126:13642.
[16] Hu J, Gao L, Zhu Y L, Wang P Y, Lin Y, Sun Z Y, Yang S, Wang Q. Chem. Eur. J., 2017, 23:1422.
[17] Song B, Liu B, Jin Y Z, He X X, Tang D T, Wu G L, Yin S C. Nanoscale, 2015, 7:930.
[18] Brizard A, Aimé C, Labrot T, Huc I, Berthier D, Artzner F, Desbat B, Oda R. J. Am. Chem. Soc., 2007, 129:3754.
[19] Gopal A, Hifsudheen M, Furumi S, Takeuchi M, Ajayaghosh A. Angew. Chem. Int. Ed., 2012, 51:10505.
[20] 黄磊(Huang L), 黄通(Huang T), 白永平(Bai Y P), 周永丰(Zhou Y F). 化学学报(Acta Chimica Sinica), 2016, 74(12):990.
[21] Barclay T G, Constantopoulos K, Matisons J. Chem. Rev., 2014, 114:10217.
[22] Du X W, Zhou J, Shi J F, Xu B. Chem. Rev., 2015, 115:13165.
[23] Zhang L, Wang T Y, Shen Z C, Liu M H. Adv. Mater., 2016, 28:1044.
[24] 高玉霞(Gao Y X), 胡君(Hu J), 巨勇(Ju Y). 化学学报(Acta Chimica Sinica), 2016, 74(4):312.
[25] 卢金荣(Lu J R), 巨勇(Ju Y).有机化学(Chinese Journal of Organic Chemistry), 2013, 33(3):469.
[26] 卢金荣(Lu J R), 巨勇(Ju Y).化学进展(Progress in Chemistry), 2016, 28(2/3):260.
[27] Hosta-Rigau L, Zhang Y, Teo B M, Postma A, Städler B. Nanoscale, 2013, 5:89.
[28] Xu F M, Wang H B, Zhao J, Liu X S, Li D D, Chen C J, Ji J. Macromolecules, 2013, 46:4235.
[29] 胡方振(Hu F Z), 陈圣典(Chen S D), 李慧(Li H), 孙景景(Sun J J), 盛瑞隆(Sheng R L), 罗挺(Luo T), 曹阿民(Cao A M). 化学学报(Acta Chimica Sinica), 2013, 71(3):351.
[30] 薛翠花(Xue C H), 牟其明(Mu Q M), 陈淑华(Chen S H). 化学学报(Acta Chimica Sinica), 2002, 60(2):355.
[31] Ono Y, Nakashima K, Sano M, Hojo J, Shinkai S. J. Mater. Chem., 2001, 11:2412.
[32] Ajayaghosh A, Vijayakumar C, Varghese R, George S J. Angew. Chem. Int. Ed., 2006, 45:456.
[33] Vedhanarayanan B, Nair V S, Nair V C, Ajayaghosh A. Angew. Chem. Int. Ed., 2016, 55:10345.
[34] Tu T, Fang W W, Bao X L, Li X B, Dötz K H. Angew. Chem. Int. Ed., 2011, 50:6601.
[35] Mao Y Y, Liu K Y, Meng L Y, Chen L, Chen L M, Yi T. Soft Matter, 2014, 10:7615.
[36] Sánchez-Ferrer A, Adamcik J, Mezzenga R. Soft Matter, 2012, 8:149.
[37] 李伟娜(Li W N).清华大学博士论文(Doctoral Dissertation of Tsinghua University), 2013.
[38] 张荷兰(Zhang H L), 彭军霞(Peng J X), 刘凯强(Liu K Q), 房喻(Fang Y). 化学进展(Progress in Chemistry), 2011, 23(8):1591.
[39] Schefer L, Sánchez-Ferrer A, Adamcik J, Mezzenga R. Langmuir, 2012, 28:5999.
[40] Ramanathan N, Currie A L, Colvin J R. Nature, 1961, 190:779.
[41] Terech P, Talmon Y. Langmuir, 2002, 18:7240.
[42] Jean B, Oss-Romen L, Terech P, Talmon Y. Adv. Mater., 2005, 17:728.
[43] Zhang X J, Zou J H, Tamhane K, Kobzeff F F, Fang J Y. Small, 2010, 6:217.
[44] Tamhane K, Zhang X J, Zou J H, Fang J Y. Soft Matter, 2010, 6:1224.
[45] Zhang X J, Tamhane K, Bera T, Fang J. J. Mater. Chem., 2011, 21:13973.
[46] Qiao Y, Lin Y Y, Wang Y J, Yang Z Y, Liu J, Zhou J, Yan Y, Huang J B. Nano Lett., 2009, 9:4500.
[47] Travaglini L, D'Annibale A, Schillén K, Olsson U, Sennato S, Pavel N V, Galantini L. Chem. Commun., 2012, 48:12011.
[48] Li Y, Li G T, Wang X Y, Li W N, Su Z X, Zhang Y H, Ju Y. Chem. Eur. J., 2009, 15:6399.
[49] Hu J, Zhang M, Ju Y. Soft Matter, 2009, 5:4971.
[50] Hu J, Wu J D, Wang Q, Ju Y. Beilstein J. Org. Chem., 2013, 9:2877.
[51] Bag B G, Dinda S K, Dey P P, Mallia A, Weiss R G. Langmuir, 2009, 25:8663.
[52] Saha A, Adamcik J, Bolisetty S, Handschin S, Mezzenga R. Angew. Chem. Int. Ed., 2015, 54:5408.
[53] Gao Y X, Hao J, Wu J D, Zhang X, Hu J, Ju Y. Langmuir, 2016, 32:1685.
[54] Gao Y X, Hao J, Wu J D, Zhang X, Hu J, Ju Y. Nanoscale, 2015, 7:13568.
[55] Gao Y X, Hao J, Wu J D, Li Y, Lin Y, Hu J, Ju Y. Soft Matter, 2016, 12:8979.
[56] Duan P F, Zhu X F, Liu M H. Chem. Commun., 2011, 47:5569.
[57] Zhang L, Liu C X, Jin Q X, Zhu X F, Liu M H. Soft Matter, 2013, 9:7966.
[58] Chen C F, Wang T Y, Fu Y Z, Liu M H. Chem. Commun., 2016, 52:1381.
[59] Wang X F, Duan P F, Liu M H. Chem. Commun., 2012, 48:7501.
[60] Zhou X Q, Jin Q X, Zhang L, Shen Z C, Jiang L, Liu M H. Small, 2016, 12:4743.
[61] Wang X F, Liu M H. Chem. Eur. J., 2014, 20:10110.
[62] Lv K, Zhang L, Liu M H. Langmuir, 2014, 30:9295.
[63] Wang X F, Duan P F, Liu M H. Chem. Eur. J., 2013, 19:16072.
[64] Jiang J, Wang T Y, Liu M H. Chem. Commun., 2010, 46:7178.
[65] Jiang J, Meng Y, Zhang L, Liu M H. J. Am. Chem. Soc., 2016, 138:15629.
[66] Deng M, Zhang L, Jiang Y Q, Liu M H. Angew. Chem. Int. Ed., 2016, 55:15062.
[67] Ziserman L, Lee H Y, Raghavan S R, Mor A, Danino D. J. Am. Chem. Soc., 2011, 133:2511.
[68] Wu X J, Ji S J, Li Y, Li B Z, Zhu X L, Hanabusa K, Yang Y G. J. Am. Chem. Soc., 2009, 131:5986.
[69] Zhang C Y, Wang S B, Huo H J, Li Y, Li B Z, Yang Y G. Mater. Lett., 2012, 88:23.
[70] Zhang C Y, Huo H J, Li Y, Li B Z, Yang Y G. Mater. Lett., 2013, 102-103:50.
[71] Zhang C Y, Wang S B, Huo H J, Huang Z B, Li Y, Li B Z, Yang Y G. Chem. Asian. J., 2013, 8:709.
[72] Levi G, Scolnik Y, Mastai Y. ACS Appl. Mater. Inter., 2016, 8:23356.
[73] Liu G F, Zhu L Y, Ji W, Feng C L, Wei Z X. Angew. Chem. Int. Ed., 2016, 55:2411.
[74] Wang Y F, Qi W, Huang R L, Yang X J, Wang M F, Su R X, He Z M. J. Am. Chem. Soc., 2015, 137:7869.
[75] Lin Y Y, Pashuck E T, Thomas M R, Amdursky N, Wang S T, Chow L W, Stevens M. M. Angew. Chem. Int. Ed., 2017, 56:2361.
[76] Chabre Y M, Roy R. Chem. Soc. Rev., 2013, 42:4657.
[77] Wang K R, Han D, Cao G J, Li X L. Chem. Asian J., 2015, 10:1204.
[78] 王克让(Wang K R). 化学进展(Progress in Chemistry), 2015, 27(6):775.
[79] Hu J C, Kuang W F, Deng K, Zou W J, Huang Y W, Wei Z X, Faul C F J. Adv. Funct. Mater., 2012, 22:4149.
[80] Yang Y, Zhang Y J, Wei Z X. Adv. Mater., 2013, 25:6039.
[81] Huang Y W, Hu J C, Kuang W F, Wei Z X, Faul C F J. Chem. Commun., 2011, 47:5554.
[82] Sun K, Xiao C Y, Liu C M, Fu W X, Wang Z H, Li Z B. Langmuir, 2014, 30:11040.
[83] Wang K R, An H W, Wu L, Zhang J C, Li X L. Chem. Commun., 2012, 48:5644.
[84] Ogawa Y, Yoshiyama C, Kitaoka T. Langmuir, 2012, 28:4404.
[85] Cui J X, Liu A H, Guan Y, Zheng J, Shen Z H, Wan X H. Langmuir, 2010, 26:3615.
[86] Clemente M J, Fitremann J, Mauzac M, Serrano J L, Oriol L. Langmuir, 2011, 27:15236.
[87] Clemente M J, Romero P, Serrano J L, Fitremann J, Oriol L. Chem. Mater., 2012, 24:3847.
[88] Jung J H, Do Y, Lee Y A, Shimizu T. Chem. Eur. J., 2005, 11:5538.
[89] Li J J, Fan K Q, Guan X D, Yu Y Z, Song J. Langmuir, 2014, 30:13422.
[90] Oda K, Huc I, Candau S J. Angew. Chem. Int. Ed., 1998, 37:2689.
[91] Delclos T, Aimé C, Pouget E, Brizard A, Huc I, Delville M H, Oda R. Nano Lett., 2008, 8:1929.
[92] Das R K, Zouani O F, Labrugère C, Oda R, Durrieu M C. ACS Nano, 2013, 7:3351.
[93] Yoshi Y, Hoshino N, Tekeda T, Moritomo H, Kawamata J, Nakamura T, Akutagawa T. Chem. Eur. J., 2014, 20:16279.
[94] Ma M F, Xing P Y, Xu S G, Li S Y, Chu X X, Hao A Y. RSC Adv., 2014, 4:42372.
[95] Saha A, Manna S, Nandi A K. Langmuir, 2007, 23:13126.
[96] Bairi P, Chakraborty P, Mondal S, Roy B, Nandi A K. Soft Matter, 2014, 10:5114.
[1] 李良春, 郑仁林, 黄毅, 孙荣琴. 多组分自组装小分子水凝胶中的自分类组装[J]. 化学进展, 2023, 35(2): 274-286.
[2] 刘晓珺, 秦朗, 俞燕蕾. 胆甾相液晶螺旋方向的光调控[J]. 化学进展, 2023, 35(2): 247-262.
[3] 于兰, 薛沛然, 李欢欢, 陶冶, 陈润锋, 黄维. 圆偏振发光性质的热活化延迟荧光材料及电致发光器件[J]. 化学进展, 2022, 34(9): 1996-2011.
[4] 王萌, 宋贺, 李烨文. 三维自组装蓝相液晶光子晶体[J]. 化学进展, 2022, 34(8): 1734-1747.
[5] 蒋茹, 刘晨旭, 杨平, 游书力. 手性催化与合成中的一些凝聚态化学问题[J]. 化学进展, 2022, 34(7): 1537-1547.
[6] 韩冬雪, 金雪, 苗碗根, 焦体峰, 段鹏飞. 超分子组装体激发态手性的响应性[J]. 化学进展, 2022, 34(6): 1252-1262.
[7] 尹航, 李智, 郭晓峰, 冯岸超, 张立群, 汤华燊. RAFT链转移剂的选用原则及通用型RAFT链转移剂[J]. 化学进展, 2022, 34(6): 1298-1307.
[8] 刘玉玲, 胡腾达, 李伊莲, 林洋, Borsali Redouane, 廖英杰. 嵌段共聚物薄膜快速自组装方法[J]. 化学进展, 2022, 34(3): 609-615.
[9] 李红, 史晓丹, 李洁龄. 肽自组装水凝胶的制备及在生物医学中的应用[J]. 化学进展, 2022, 34(3): 568-579.
[10] 汤波, 王微, 罗爱芹. 新型多孔材料用作色谱手性固定相[J]. 化学进展, 2022, 34(2): 328-341.
[11] 李彬, 于颖, 幸国香, 邢金峰, 刘万兴, 张天永. 手性无机纳米材料圆偏振发光的研究进展[J]. 化学进展, 2022, 34(11): 2340-2350.
[12] 宋路杰, 吴友平, 邓建平. 手性药物的对映体选择性释放[J]. 化学进展, 2021, 33(9): 1550-1559.
[13] 冯业娜, 刘书河, 张书博, 薛彤, 庄鸿麟, 冯岸超. 基于聚合诱导自组装制备二氧化硅/聚合物纳米复合材料[J]. 化学进展, 2021, 33(11): 1953-1963.
[14] 闫楚璇, 李青璘, 巩正奇, 陈颖芝, 王鲁宁. 纳米有机半导体光催化剂[J]. 化学进展, 2021, 33(11): 1917-1934.
[15] 王子瑄, 王跃飞, 齐崴, 苏荣欣, 何志敏. DNA-多肽复合分子的设计、组装与应用[J]. 化学进展, 2020, 32(6): 687-697.