CAS: 28540-82-1; Tentoxin

该化合物是一种以其植物毒性特性而闻名的真菌Alternaria tenuis生产出的甲酸毒素,其特征是它能够抑制植物中的光合作用,导致氯化和坏死,从而严重影响植物健康和作物产量; 丁诺毒素是一种环虫酸,其结构包括一种独特的氨基酸安排,有助于其生物活动; 它溶于有机溶剂,有助于其与细胞膜和生物系统的互动; 该化合物因其可能对食品安全和植物病理产生影响而引起农业和毒理学研究的注意; 此外, 寄生毒素的动作方式涉及干扰叶片中的电子运输链,使它成为植物防御机制和真菌毒素生态影响研究的一个主题; 与许多植毒剂一样,在处理寄生毒素时,由于它对人类和动物的潜在毒性,在处理寄生毒素时,必须采取安全措施.

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CAS号35661-60-0 Fm°C-L-亮氨酸

合成工艺路线路线简述

    📜在 N,N'-二叔丁基碳二亚胺,1-羟基苯并三唑,N,N-二异丙基乙胺体系中,用 二氯甲烷,N,N-二甲基甲酰胺 用作溶剂,化学反应 1.5H,反应生成腾毒素
    参考文献:Tentoxin As A Scaffold For Drug Discovery. Total Solid-Phase Synthesis Of Tentoxin And A Library Of Analogues
    标题:Tentoxin As A Scaffold For Drug Discovery. Total Solid-Phase Synthesis Of Tentoxin And A Library Of Analogues
    摘要:[graphics]A Solid-Phase Method For The Synthesis Of Tentoxin Has Been Developed. Two Key Steps-Dehydration And Malkylation-Are Carried Out While The Peptide Is Anchored To The Resin. The Method,Which Has Been Validated By The Preparation Of A Library Of Tentoxin Analogues,Should Be Applicable To The Generation Of Further Libraries That Have The Tentoxin Scaffold Structure,As Well As Other Structures Containing N-Alkylated Didehydroamino Acids.
    Doi:10.1021/ol0345273

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    专利信息


    专利号:US-11919928-B2
    优先权日:2016-03-16
    标题 :Method for producing dihydrotentoxin
    发明人：KUBO TAKASHI; MACHIDA MASAYUKI; FUJIOKA TOMONORI; YAMAGUCHI Shigenari; KAWAI KIYOSHI
    权利人:KUMIAI CHEMICAL INDUSTRY CO
    摘要:An object of the present invention is to identify an enzyme having activity of synthesizing dihydrotentoxin that is a tentoxin precursor and an enzyme having activity of synthesizing tentoxin using dihydrotentoxin as a substrate. The present invention concerns a tentoxin synthesis-related gene encoding a protein comprising the amino acid sequence of SEQ ID NO: 16 and having activity of nonribosomal peptide synthesis of dihydrotentoxin and a tentoxin synthesis-related gene encoding a protein comprising the amino acid sequence of SEQ ID NO: 18 and having activity of converting dihydrotentoxin to tentoxin.

    专利号:AR-107900-A1
    优先权日:2016-03-16
    标题 :A SYNTHESIS GENE OF TENTOXIN, A METHOD FOR PRODUCING THENTROXINE OR DIHYDROTENTOXINE USING THE GENE, AND A TRANSFORMANT THAT UNDERSTANDS IT

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    主要参考文献


    1: Tucker WC, Du Z, Hein R, Richter ML, Gromet-Elhanan Z. Hybrid Rhodospirillum rubrum F(0)F(1) ATP synthases containing spinach chloroplast F(1) beta or alpha and beta subunits reveal the essential role of the alpha subunit in ATP synthesis and tentoxin sensitivity. J Biol Chem. 2000 Jan 14;275(2):906-12. doi: 10.1016/j.fct.2013.07.047. Epub 2013 Jul 29. Review.
    5: Pinet E, Cavelier F, Verducci J, Girault G, Dubart L, Haraux F, Sigalat C, André F. Synthesis, structure, and properties of MeSer1-tentoxin, a new cyclic tetrapeptide which interacts specifically with chloroplast F1 H(+)-ATPase differentiation of inhibitory and stimulating effects. Biochemistry. 1996 Oct 1;35(39):12804-11. Epub 2002 Apr 9. Epub 2002 Oct 23.
    17: Pavlova P, Shimabukuro K, Hisabori T, Groth G, Lill H, Bald D. Complete inhibition and partial Re-activation of single F1-ATPase molecules by tentoxin: new properties of the re-activated enzyme. J Biol Chem. 2004 Mar 12;279(11):9685-8. Epub 2004 Jan 22.

    合成参考文献


    参考文献:10.1111/mpp.12329
    摘要:De Bruyne L, Van Poucke C, Di Mavungu DJ, Zainudin NAIM, Vanhaecke L, De Vleesschauwer D, Turgeon BG, De Saeger S, Höfte M. Comparative chemical screening and genetic analysis reveal tentoxin as a new virulence factor in C ochliobolus miyabeanus , the causal agent of brown spot disease on rice. Molecular Plant Pathology. 2015 Dec;17(6):805–17. doi: 10.1111/mpp.12329.
    参考文献:10.1074/jbc.272.9.5457
    摘要:Hu D, Fiedler HR, Golan T, Edelman M, Strotmann H, Shavit N, Leu S. Catalytic Properties and Sensitivity to Tentoxin of Chlamydomonas reinhardtii ATP Synthases Changed in Codon 83 of atpB by Site-directed Mutagenesis. Journal of Biological Chemistry. 1997 Feb;272(9):5457–63. doi: 10.1074/jbc.272.9.5457.
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