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天蚕素A及相关肽的固相合成

Solid-phase synthesis of cecropin A and related peptides.

作者信息

Andreu D, Merrifield R B, Steiner H, Boman H G

出版信息

Proc Natl Acad Sci U S A. 1983 Nov;80(21):6475-9. doi: 10.1073/pnas.80.21.6475.

DOI:10.1073/pnas.80.21.6475
PMID:6579533
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC390136/
Abstract

Cecropin A, a 37-residue antibacterial peptide amide, was synthesized by the solid-phase method. It was shown to be homogeneous and totally indistinguishable from natural cecropin A by chemical and physical criteria, as well as by its antibacterial activity against several Gram-positive and Gram-negative organisms. The synthetic material was also used to establish unambiguously that the carboxyl-terminal blocking group of natural cecropin A is a primary amide as tentatively proposed earlier. The role of the amino terminus of cecropin A in antibacterial activity was investigated by the synthesis of two analogs.

摘要

天蚕素A是一种由37个氨基酸残基组成的抗菌肽酰胺,采用固相法合成。通过化学、物理标准以及对几种革兰氏阳性菌和革兰氏阴性菌的抗菌活性表明,合成的天蚕素A是均一的,与天然天蚕素A完全没有区别。合成材料还被用于明确证实天然天蚕素A的羧基末端封闭基团是一个伯酰胺,这与之前初步推测的一致。通过合成两种类似物研究了天蚕素A氨基末端在抗菌活性中的作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4240/390136/786314838d6f/pnas00647-0053-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4240/390136/3b065d6f78b4/pnas00647-0052-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4240/390136/786314838d6f/pnas00647-0053-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4240/390136/3b065d6f78b4/pnas00647-0052-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4240/390136/786314838d6f/pnas00647-0053-a.jpg

相似文献

1
Solid-phase synthesis of cecropin A and related peptides.天蚕素A及相关肽的固相合成
Proc Natl Acad Sci U S A. 1983 Nov;80(21):6475-9. doi: 10.1073/pnas.80.21.6475.
2
N-terminal analogues of cecropin A: synthesis, antibacterial activity, and conformational properties.天蚕素A的N端类似物:合成、抗菌活性及构象性质
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3
Synthesis of the antibacterial peptide cecropin A (1-33).抗菌肽天蚕素A(1 - 33)的合成
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4
The chemical synthesis of cecropin D and an analog with enhanced antibacterial activity.杀菌肽D及其具有增强抗菌活性的类似物的化学合成。
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All-D amino acid-containing channel-forming antibiotic peptides.含全D-氨基酸的形成通道的抗生素肽。
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Effects on electrophoretic mobility and antibacterial spectrum of removal of two residues from synthetic sarcotoxin IA and addition of the same residues to cecropin B.从合成的肌肉毒素IA中去除两个残基并将相同残基添加到天蚕素B对电泳迁移率和抗菌谱的影响。
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本文引用的文献

1
Insect immunity. Purification and properties of three inducible bactericidal proteins from hemolymph of immunized pupae of Hyalophora cecropia.昆虫免疫。天蚕免疫蛹血淋巴中三种诱导型杀菌蛋白的纯化及特性
Eur J Biochem. 1980 May;106(1):7-16. doi: 10.1111/j.1432-1033.1980.tb05991.x.
2
Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction.通过茚三酮反应对固相肽合成进行定量监测。
Anal Biochem. 1981 Oct;117(1):147-57. doi: 10.1016/0003-2697(81)90704-1.
3
Insect immunity: isolation and structure of cecropin D and four minor antibacterial components from Cecropia pupae.
天蚕素A-蜂毒素杂合肽N端插入单个色氨酸如何改变其抗菌和生物物理特性
Membranes (Basel). 2021 Jan 12;11(1):48. doi: 10.3390/membranes11010048.
4
Control of Citrus Post-harvest Green Molds, Blue Molds, and Sour Rot by the Cecropin A-Melittin Hybrid Peptide BP21.天蚕素A-蜂毒素杂合肽BP21对柑橘采后绿霉病、青霉病和酸腐病的控制
Front Microbiol. 2018 Oct 10;9:2455. doi: 10.3389/fmicb.2018.02455. eCollection 2018.
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Rapid and efficient production of cecropin A antibacterial peptide in Escherichia coli by fusion with a self-aggregating protein.通过与自聚集蛋白融合,在大肠杆菌中快速高效生产抗菌肽 Cecropin A。
BMC Biotechnol. 2018 Oct 5;18(1):62. doi: 10.1186/s12896-018-0473-7.
6
Activity of AMP2041 against human and animal multidrug resistant Pseudomonas aeruginosa clinical isolates.AMP2041对人源和动物源多重耐药铜绿假单胞菌临床分离株的活性。
Ann Clin Microbiol Antimicrob. 2017 Mar 23;16(1):17. doi: 10.1186/s12941-017-0193-1.
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Highly potent antimicrobial peptides from N-terminal membrane-binding region of E. coli MreB.来自大肠杆菌 MreB N 端膜结合区的高效抗菌肽。
Sci Rep. 2017 Feb 23;7:42994. doi: 10.1038/srep42994.
8
Constitutive expression of a novel antimicrobial protein, Hcm1, confers resistance to both Verticillium and Fusarium wilts in cotton.一种新型抗菌蛋白Hcm1的组成型表达赋予棉花对黄萎病和枯萎病的抗性。
Sci Rep. 2016 Feb 9;6:20773. doi: 10.1038/srep20773.
9
Antimicrobial cyclic peptides for plant disease control.用于植物病害防治的抗菌环肽。
Plant Pathol J. 2015 Mar;31(1):1-11. doi: 10.5423/PPJ.RW.08.2014.0074. Epub 2015 Mar 31.
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Distinct profiling of antimicrobial peptide families.抗菌肽家族的独特图谱分析。
Bioinformatics. 2015 Mar 15;31(6):849-56. doi: 10.1093/bioinformatics/btu738. Epub 2014 Nov 10.
昆虫免疫:从天蚕蛹中分离出杀菌肽D及四种次要抗菌成分并解析其结构
Eur J Biochem. 1982 Sep;127(1):207-17. doi: 10.1111/j.1432-1033.1982.tb06857.x.
4
Weak acid-catalyzed pyrrolidone carboxylic acid formation from glutamine during solid phase peptide synthesis. Minimization by rapid coupling.在固相肽合成过程中,谷氨酰胺经弱酸催化形成吡咯烷酮羧酸。通过快速偶联使其最小化。
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Humoral immunity in Cecropia pupae.天蚕蛹中的体液免疫。
Curr Top Microbiol Immunol. 1981;94-95:75-91. doi: 10.1007/978-3-642-68120-2_2.
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Sequence and specificity of two antibacterial proteins involved in insect immunity.参与昆虫免疫的两种抗菌蛋白的序列与特异性
Nature. 1981 Jul 16;292(5820):246-8. doi: 10.1038/292246a0.
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Eur J Biochem. 1982 Sep;127(1):219-24. doi: 10.1111/j.1432-1033.1982.tb06858.x.
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EMBO J. 1983;2(4):571-6. doi: 10.1002/j.1460-2075.1983.tb01465.x.
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[A new method for synthesis of peptides: activation of the carboxyl group with dicyclohexylcarbodiimide using 1-hydroxybenzotriazoles as additives].[一种合成肽的新方法:以1-羟基苯并三唑为添加剂,用二环己基碳二亚胺活化羧基]
Chem Ber. 1970;103(3):788-98. doi: 10.1002/cber.19701030319.