Citation: YANG Jin, MA Qiseng, ZHONG Ying, ZHU Longbao, GE Fei, TAO Yugui, SONG Ping. Solid-Phase Synthesis of Cyclohexapeptide Thermoactinoamide A and Its Antibacterial Activity[J]. Chinese Journal of Applied Chemistry, ;2019, 36(6): 677-682. doi: 10.11944/j.issn.1000-0518.2019.06.180364 shu

Solid-Phase Synthesis of Cyclohexapeptide Thermoactinoamide A and Its Antibacterial Activity

School of Biochemical Engineering, Anhui Polytechnic University, Wuhu, Anhui 241000, China

Corresponding author: ZHU Longbao, swgctaoyg@126.com
Received Date: 13 November 2018
Revised Date: 19 December 2018
Accepted Date: 30 January 2019

Fund Project: the Natural Sciences Foundation of Anhui Province Universities KJ2017A123the Anhui Polytechnic University Youth Talent Program 2016BJRC006Supported by the Natural Sciences Foundation of Anhui Province Universities(No.KJ2017A123), the Anhui Polytechnic University Youth Talent Program(No.2016BJRC006)

Figures(2)

A natural antibacterial cyclic peptide thermoactinoamide A was synthesized by solid-liquid phase two-step method. First, based on fluorenylmethoxycarbonyl(Fmoc) solid phase synthesis, the linear peptide was obtained in 84% yield by optimizing the addition of N, N'-diisopropylethylamine(DIPEA). Then the linear peptide was converted to thermoactinoamide A in 51% yield(43% yield total) through optimizing the cyclization conditions. Antibacterial activity test results show that minimum inhibitory concentration of cyclic thermoactinoamide A for Staphylococcus aureus is 32 μg/mL. In summary, an effectively synthetic strategy was developed for further applications of cyclic peptide thermoactinoamide A on analyzing the structure-activity relationship and improving the bioactivity.
- thermoactinoamide A,
- solid-phase synthesis,
- cyclic peptide,
- antibacterial activity
1. [1]
  Stanton T B. A Call for Antibiotic Alternatives Research[J]. Trends Microbiol, 2013,21(3):111-113. doi: 10.1016/j.tim.2012.11.002
2. [2]
  Mangoni M L, Di Grazia A, Cappiello F. Naturally Occurring Peptides from Rana temporaria:Antimicrobial Properties and More[J]. Curr Top Med Chem, 2016,16(1):54-64.
3. [3]
  O'Shea R, Moser H E. Physicochemical Properties of Antibacterial Compounds:Implications for Drug Discovery[J]. J Med Chem, 2008,51(10):2871-2878. doi: 10.1021/jm700967e
4. [4]
  Fischbach M A, Walsh C T, Walsh C T. Antibiotics for Emerging Pathogens[J]. Science, 2009,325(5944):1089-1093. doi: 10.1126/science.1176667
5. [5]
  Teta R, Marteinsson V T, Longeon A. Thermoactinoamide A, An Antibiotic Lipophilic Cyclopeptide from the Icelandic Thermophilic Bacterium Thermoactinomyces vulgaris[J]. J Nat Prod, 2017,80(9):2530-2535. doi: 10.1021/acs.jnatprod.7b00560
6. [6]
  ZHU Longbao, YANG Jin, TAO Yugui. Chemical Synthesis Method and Process of an Antibacterial Cyclic Peptide Thermoactinoamide A: CN1087155605A[P]. 2018-10-30.(in Chinese)
7. [7]
  Son S, Hong Y S, Jang M. Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species[J]. J Nat Prod, 2017,45(12):3025-3031.
8. [8]
  Song Y X, Li Q L, Liu X. Cyclic Hexapeptides from the Deep South China Sea-Derived Streptomyces scopuliridis SCIO ZJ46 Active Against Pathogenic Gram-Positive Bacteria[J]. J Nat Prod, 2014,77(8):1937-1941. doi: 10.1021/np500399v
9. [9]
  Jang J P, Nogawa T, Futamra Y. Octaminomycins A and B, Cyclic Octadepsipeptides Active Against Plasmodium falciparum[J]. J Nat Prod, 2017,80(1):134-140. doi: 10.1021/acs.jnatprod.6b00758
10. [10]
  Pfaller M A, Andes D, Diekema D J. Wild-Type MIC Distributions, Epidemiological Cutoff Values and Species-Specific Clinical Breakpoints for Fluconazole and Candida:Time for Harmonization of CLSI and EUCAST Broth Microdilution Methods[J]. Drug Resist Updates, 2010,13(6):180-195. doi: 10.1016/j.drup.2010.09.002
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Wan Li , Mei Shi , Yanping Ren , Faqiong Zhao , Min Hu , Xiuyun Wang , Juanjuan Song , Yongxian Fan , Dongcheng Liu , Xiuqiong Zeng , Wenwei Zhang , Weihong Li , Xiaohang Qiu , Yong Fan , Jianrong Zhang , Shuyong Zhang . Suggestions on Heating and Heating Instruments (Part V): Solid-State Synthesis and High-Temperature Heating Using Muffle and Tube Furnaces. University Chemistry, 2026, 41(3): 182-190. doi: 10.12461/PKU.DXHX202507046
3. [3]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
4. [4]
  Jia JI , Tengqi YAO , Wenqian DENG , Wenjing SHI , Xuan LÜ , Lin TIAN , Xiaoyan XIN , Yinling HOU . Structures, antibacterial activities, and interactions with DNA of two nickel complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 78-86. doi: 10.11862/CJIC.20250141
5. [5]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
6. [6]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
7. [7]
  Xiaohang JIN , Qi LIU , Jianping LANG . Room‑temperature solid‑state synthesis, structure, and third‑order nonlinear optical properties of phosphine‑ligand‑protected silver thiolate clusters. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1505-1512. doi: 10.11862/CJIC.20250125
8. [8]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
9. [9]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
10. [10]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
11. [11]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
12. [12]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
13. [13]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
14. [14]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
15. [15]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
16. [16]
  Chongjing Liu , Yujian Xia , Pengjun Zhang , Shiqiang Wei , Dengfeng Cao , Beibei Sheng , Yongheng Chu , Shuangming Chen , Li Song , Xiaosong Liu . Understanding Solid-Gas and Solid-Liquid Interfaces through Near Ambient Pressure X-Ray Photoelectron Spectroscopy. Acta Physico-Chimica Sinica, 2025, 41(2): 100013-0. doi: 10.3866/PKU.WHXB202309036
17. [17]
  Chunai Dai , Yongsheng Han , Luting Yan , Zhen Li , Yingze Cao . Ideological and Political Design of Solid-liquid Contact Angle Measurement Experiment. University Chemistry, 2024, 39(2): 28-33. doi: 10.3866/PKU.DXHX202306065
18. [18]
  Fang Niu , Rong Li , Qiaolan Zhang . Analysis of Gas-Solid Adsorption Behavior in Resistive Gas Sensing Process. University Chemistry, 2024, 39(8): 142-148. doi: 10.3866/PKU.DXHX202311102
19. [19]
  Xianglan Zhang , Jingwen Ma , Junya Cao , Weibin Cai , Zhibing Chang , Jinchang Liu . “价值引领，固基强能”的化工原理教改与实践. University Chemistry, 2025, 40(8): 11-17. doi: 10.12461/PKU.DXHX202410041
20. [20]
  Siwei Hou , Yaxin Niu , Guanglu Zhang , Yanmei Yang , Xu Wang , Zhenzhen Chen . Application of Solid-Phase Microextraction and Mass Spectrometry in Environmental Detection. University Chemistry, 2026, 41(3): 297-306. doi: 10.12461/PKU.DXHX202504078

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1248)
HTML views(177)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142