一种替考拉宁类似物的X射线晶体学结构揭示了替考拉宁药效团的关键相互作用。
X-ray crystallographic structure of a teixobactin analogue reveals key interactions of the teixobactin pharmacophore.
作者信息
Yang H, Du Bois D R, Ziller J W, Nowick J S
机构信息
Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025, USA.
出版信息
Chem Commun (Camb). 2017 Feb 28;53(18):2772-2775. doi: 10.1039/c7cc00783c.
Abstract
The X-ray crystallographic structure of a truncated teixobactin analogue reveals hydrogen-bonding and hydrophobic interactions and a cavity that binds a chloride anion. Minimum inhibitory concentration (MIC) assays against Gram-positive bacteria correlate the observed structure with antibiotic activity.
摘要
截短的替考拉宁类似物的X射线晶体结构揭示了氢键和疏水相互作用以及一个结合氯离子阴离子的空腔。针对革兰氏阳性菌的最低抑菌浓度（MIC）测定将观察到的结构与抗生素活性相关联。
相似文献
1
X-ray crystallographic structure of a teixobactin analogue reveals key interactions of the teixobactin pharmacophore.一种替考拉宁类似物的X射线晶体学结构揭示了替考拉宁药效团的关键相互作用。
Chem Commun (Camb). 2017 Feb 28;53(18):2772-2775. doi: 10.1039/c7cc00783c.
2
Elucidation of the Teixobactin Pharmacophore.替考拉宁药效基团的阐明。
ACS Chem Biol. 2016 Jul 15;11(7):1823-6. doi: 10.1021/acschembio.6b00295. Epub 2016 Jun 3.
3
Developing Equipotent Teixobactin Analogues against Drug-Resistant Bacteria and Discovering a Hydrophobic Interaction between Lipid II and Teixobactin.开发针对耐药菌的等效替考拉宁类似物，并发现脂质 II 与替考拉宁之间的疏水相互作用。
J Med Chem. 2018 Apr 26;61(8):3409-3421. doi: 10.1021/acs.jmedchem.7b01241. Epub 2018 Apr 13.
4
Chemistry and Biology of Teixobactin.泰妙菌素的化学与生物学。
Chemistry. 2018 Apr 11;24(21):5406-5422. doi: 10.1002/chem.201704167. Epub 2017 Dec 12.
5
Synthesis and antibacterial studies of teixobactin analogues with non-isostere substitution of enduracididine.泰妙菌素类似物的合成及非等排取代延胡索氨酸的抗菌研究。
Bioorg Med Chem. 2018 Mar 1;26(5):1062-1068. doi: 10.1016/j.bmc.2018.01.016. Epub 2018 Feb 1.
6
Dissecting the Binding Interactions of Teixobactin with the Bacterial Cell-Wall Precursor Lipid II.解析 Teixobactin 与细菌细胞壁前体脂质 II 的结合相互作用。
Chembiochem. 2020 Mar 16;21(6):789-792. doi: 10.1002/cbic.201900504. Epub 2019 Nov 12.
7
A Fluorescent Teixobactin Analogue.一种荧光泰妙菌素类似物。
ACS Chem Biol. 2020 May 15;15(5):1222-1231. doi: 10.1021/acschembio.9b00908. Epub 2020 Feb 26.
8
Rational Design and Synthesis of Modified Teixobactin Analogues: In Vitro Antibacterial Activity against Staphylococcus aureus, Propionibacterium acnes and Pseudomonas aeruginosa.经理性设计和泰妙菌素类似物的合成：对金黄色葡萄球菌、痤疮丙酸杆菌和铜绿假单胞菌的体外抗菌活性。
Chemistry. 2018 Jun 26;24(36):9136-9147. doi: 10.1002/chem.201801423. Epub 2018 Jun 6.
9
Teixobactin and Its Analogues: A New Hope in Antibiotic Discovery.替考拉宁及其类似物：抗生素发现中的新希望。
ACS Infect Dis. 2017 Oct 13;3(10):688-690. doi: 10.1021/acsinfecdis.7b00108. Epub 2017 Aug 3.
10
Design, Synthesis, and Study of Lactam and Ring-Expanded Analogues of Teixobactin.替考拉宁的内酰胺和扩环类似物的设计、合成与研究
J Org Chem. 2020 Feb 7;85(3):1331-1339. doi: 10.1021/acs.joc.9b02631. Epub 2019 Dec 9.
引用本文的文献
1
Structure-Activity Relationship Studies of the Peptide Antibiotic Clovibactin.肽抗生素克洛维巴坦的结构-活性关系研究。
J Org Chem. 2024 Sep 6;89(17):12479-12484. doi: 10.1021/acs.joc.4c01414. Epub 2024 Aug 23.
2
Supramolecular Interactions of Teixobactin Analogues in the Crystal State.替考拉宁类似物在晶体状态下的超分子相互作用
J Org Chem. 2024 Apr 5;89(7):5104-5108. doi: 10.1021/acs.joc.3c02617. Epub 2024 Mar 20.
3
New Teixobactin Analogues with a Total Lactam Ring.具有完整内酰胺环的新型替考拉宁类似物。
ACS Med Chem Lett. 2023 Nov 14;14(12):1827-1832. doi: 10.1021/acsmedchemlett.3c00435. eCollection 2023 Dec 14.
4
Synthesis and Stereochemical Determination of the Peptide Antibiotic Novo29.新型 29 号肽抗生素的合成与立体化学测定。
J Org Chem. 2023 Feb 17;88(4):2214-2220. doi: 10.1021/acs.joc.2c02648. Epub 2023 Jan 19.
5
Isobactins: -acyl isopeptide prodrugs of teixobactin and teixobactin derivatives.异杆菌素：替考拉宁及其衍生物的酰基异肽前药。
Chem Sci. 2022 Oct 24;13(44):13110-13116. doi: 10.1039/d2sc02670h. eCollection 2022 Nov 16.
6
Linearized teixobactin is inactive and after sequence enhancement, kills methicillin-resistant Staphylococcus aureus via a different mechanism.线性化的替考拉宁无活性，在序列增强后，通过不同机制杀死耐甲氧西林金黄色葡萄球菌。
Pept Sci (Hoboken). 2022 Sep;114(5). doi: 10.1002/pep2.24269. Epub 2022 Apr 25.
7
Computer-Aided Drug Design Boosts RAS Inhibitor Discovery.计算机辅助药物设计助力 RAS 抑制剂的发现。
Molecules. 2022 Sep 5;27(17):5710. doi: 10.3390/molecules27175710.
8
Visualizing Teixobactin Supramolecular Assemblies and Cell Wall Damage in Using CryoEM.利用冷冻电镜观察替考拉宁超分子聚集体及细胞壁损伤情况。
ACS Omega. 2021 Oct 7;6(41):27412-27417. doi: 10.1021/acsomega.1c04331. eCollection 2021 Oct 19.
9
Molecular Dynamics Insight into the Lipid II Recognition by Type A Lantibiotics: Nisin, Epidermin, and Gallidermin.A型羊毛硫抗生素对脂磷壁酸前体的分子动力学洞察：乳链菌肽、表皮菌素和加里德菌素
Micromachines (Basel). 2021 Sep 28;12(10):1169. doi: 10.3390/mi12101169.
10
Emerging peptide antibiotics with therapeutic potential.具有治疗潜力的新型肽类抗生素。
Med Drug Discov. 2021 Mar;9:100078. doi: 10.1016/j.medidd.2020.100078. Epub 2020 Dec 30.
本文引用的文献
1
Lysine Scanning of Arg-Teixobactin: Deciphering the Role of Hydrophobic and Hydrophilic Residues.精氨酸-替考拉宁的赖氨酸扫描：解读疏水和亲水残基的作用
ACS Omega. 2016 Dec 31;1(6):1262-1265. doi: 10.1021/acsomega.6b00354. Epub 2016 Dec 19.
2
Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis.持久氨酸，一种肽类抗生素中的稀有氨基酸成分：天然产物与合成
Beilstein J Org Chem. 2016 Nov 7;12:2325-2342. doi: 10.3762/bjoc.12.226. eCollection 2016.
3
Defining the molecular structure of teixobactin analogues and understanding their role in antibacterial activities.确定替考拉宁类似物的分子结构并了解它们在抗菌活性中的作用。
Chem Commun (Camb). 2017 Feb 7;53(12):2016-2019. doi: 10.1039/c6cc09490b.
4
Dual Targeting of Cell Wall Precursors by Teixobactin Leads to Cell Lysis.替考拉宁对细胞壁前体的双重靶向作用导致细胞裂解。
Antimicrob Agents Chemother. 2016 Oct 21;60(11):6510-6517. doi: 10.1128/AAC.01050-16. Print 2016 Nov.
5
Total synthesis of teixobactin.泰妙菌素的全合成。
Nat Commun. 2016 Aug 3;7:12394. doi: 10.1038/ncomms12394.
6
Elucidation of the Teixobactin Pharmacophore.替考拉宁药效基团的阐明。
ACS Chem Biol. 2016 Jul 15;11(7):1823-6. doi: 10.1021/acschembio.6b00295. Epub 2016 Jun 3.
7
Total Synthesis of Teixobactin.泰妙菌素的全合成。
Org Lett. 2016 Jun 3;18(11):2788-91. doi: 10.1021/acs.orglett.6b01324. Epub 2016 May 18.
8
Efficient total syntheses and biological activities of two teixobactin analogues.两种替考拉宁类似物的高效全合成及生物活性
Chem Commun (Camb). 2016 Apr 26;52(36):6060-3. doi: 10.1039/c5cc10249a.
9
Synthesis and Biological Evaluation of a Teixobactin Analogue.泰妙菌素类似物的合成与生物评价。
Org Lett. 2015 Dec 18;17(24):6182-5. doi: 10.1021/acs.orglett.5b03176. Epub 2015 Dec 10.
10
A Highly Stereoselective and Scalable Synthesis of L-allo-Enduracididine.L-allo-烯丙基精氨酸的高对映选择性和可扩展性合成。
Org Lett. 2015 Sep 18;17(18):4620-3. doi: 10.1021/acs.orglett.5b02362. Epub 2015 Sep 10.
Zotero 插件