CAS: 87081-35-4; (2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-Ethyl-6-Hydroxy-3,5,7,9,11,15-Hexamethyl-19-((2S,3S)-3-Methyl-6-Oxo-3,6-Dihydro-2H-Pyran-2-yl)-8-Oxononadeca-2,10,12,16,18-Pentaenoic Acid

该化合物是一种天然产品,是一种属于被称为大型硅化物的化合物类别的强效抗生素,由活性蛋白菌(Streptomyces leptomices leptophaerius)生产,其特点是能够以出口1号(XPO1)路径为目标,抑制核蛋白的出口,特别是含有核定位信号的蛋白质的出口;乳胶B对各种癌症细胞线表现出严重的细胞毒性,使其成为癌症研究的一个主题;其行动机制包括形成一个含有出口1号和货物蛋白质的复合体,从而防止其从核体转移到细胞型体.此外,乳胶B在调节免疫反应方面表现出潜力,并研究其对病毒感染的影响.该化合物通常用于实验室环境的研究目的,其独特的特性使它成为研究细胞迁移机制和肿瘤治疗应用的宝贵工具.

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合成工艺路线路线简述

  • 合成目标产物 Leptomycin B 主要起始原料 4-Pentyn-2-Ol, 3-Methyl-1-(Phenylmethoxy)-, (2R,3S)-
  • (文献来源)合成步骤主要原料 4-Pentyn-2-Ol, 3-Methyl-1-(Phenylmethoxy)-, (2R,3S)-
📜(2S,3S)-2-[(1E,3Z,5R)-3-Ethyl-7-Hydroxy-5-Methylhepta-1,3-Dienyl]-3-Methyl-2,3-Dihydropyran-6-One置于吡啶,Manganese(Iv) Oxide,Sodium Chlorite,Sodium Dihydrogenphosphate,双氧水,Dimsyl Lithium,戴斯-马丁氧化剂,氟化氢吡啶体系中,用 四氢呋喃,二氯甲烷,甲苯,乙腈,苯 作为反应溶剂,化学反应生成 来普霉素b
参考文献:Absolute Stereostructure And Total Synthesis Of Leptomycin B
标题:Absolute Stereostructure And Total Synthesis Of Leptomycin B
摘要:The Absolute Stereostructure Of Leptomycin B,An Antitumor Antibiotic And Inhibitor Of Nuclear Protein Export,Was Firstly Presumed As 1 Having 4S,5R,10R,16R,18S,19R,20S On The Basis Of NMR Comparison With Callystatin A (2) And Then 1 Was Asymmetrically Synthesized. The Synthesized Leptomycin B (I) Was Found Identical With The Authentic Sample In HPLC And Cd Comparison As Well As In Other Respects. This Structural Elucidation Of The Absolute Stereostructure And Total Synthesis Are The First Example;Among The Leptomycin Family As Streptomyces Metabolites. (C) 1998 Elsevier Science Ltd. All Rights Reserved.
DOI:10.1016/s0040-4039(98)01809-7

专利信息


专利号:US-10029014-B2
优先权日:2013-09-10
标题:Synthesis of novel asymmetric bow-tie PAMAM dendrimer-based conjugates for tumor-targeting drug delivery
发明人:OJIMA IWAO; WANG TAO; TENG YU-HAN
权利人:UNIV NEW YORK STATE RES FOUND
摘要:The present disclosure relates to a dendrimer-based conjugate of the formula V m -D-C-D′-(T-F) n , which is useful for tumor targeting drug delivery. The use of asymmetric dendrimers allow for specific targeting as well as synthetic reproducibility.

专利号:US-11946086-B2
优先权日:2017-01-05
标题 :Gene involved in synthesis of cyclic peptide compound, method for producing cyclic peptide compound using the same, and transformant comprising the same
发明人:KUBO TAKASHI; MACHIDA MASAYUKI; UMEMURA MAIKO; ABE KEIETSU; YOSHIMI AKIRA; FUJIOKA TOMONORI; YAMAGUCHI Shigenari; KAWAI KIYOSHI
权利人:AIST; UNIV TOHOKU; KUMIAI CHEMICAL INDUSTRY CO
摘要:This invention is intended to identify a gene cluster involved in biosynthesis of a cyclic peptide compound produced by a filamentous fungus of the Curvularia species and to establish a system for synthesizing such cyclic peptide compound. The gene is composed of a first module to a tenth module and encodes a protein having activity of synthesizing a nonribosomal peptide constituting a basic peptide backbone of a cyclic peptide compound produced by a filamentous fungus of the Curvularia species.

专利号:US-2022259634-A1
优先权日:2017-01-05
标题:Gene involved in synthesis of cyclic peptide compound, method for producing cyclic peptide compound using the same, and transformant comprising the same

专利号:US-11712432-B2
优先权日:2018-12-20
标题 :Method of treating cancer with an elevated glycogen content
发明人:GENTRY MATTHEW S; SUN RAMON C; YOUNG LYNDSAY EA
权利人:UNIV KENTUCKY RES FOUND
摘要:A method of treating cancer is provided. The method includes administering to a subject in need thereof an effective amount of a compound selected from the group consisting of a glycogen phosphorylase inhibitor, a glycogen synthase inhibitor, a glycogen degradation molecule, an anti-sense oligonucleotide that down-regulates glycogen synthesis, and combinations thereof, where the cancer includes elevated levels of glycogen.

专利号:CN-111684066-B
优先权日:2017-01-05
标题 :Genes related to the synthesis of cyclic peptide compounds, methods for producing cyclic peptide compounds using the genes, and transformants having the genes

专利号:US-2016220688-A1
优先权日:2013-09-10
标题:Synthesis of novel asymmetric bow-tie pamam dendrimer-based conjugates for tumor-targeting drug delivery

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品牌试剂参考报价(招募中)

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主要参考文献


1: Thirumalairaj J, Sivasankari K, Natarajaseenivasan K, Balagurunathan R. Potential anti-leptospiral compound, leptomycin B from marine Streptomyces indiaensis MSU5: taxonomy, fermentation, compound isolation, in vitro and in vivo efficacy. World J Microbiol Biotechnol. 2017 Sep 27;33(10):187. doi: 10.1007/s11274-017-2351-1. doi: 10.1016/j.taap.2017.09.017. Epub 2017 Sep 21.
3: Min SJ, Hyun HW, Kang TC. Leptomycin B attenuates neuronal death via PKA- and PP2B-mediated ERK1/2 activation in the rat hippocampus following status epilepticus. Brain Res. 2017 Sep 1;1670:14-23. doi: 10.1016/j.brainres.2017.06.002. Epub 2017 Jun 7. doi: 10.1016/j.bbrc.2017.04.042. Epub 2017 Apr 12.
5: Kim DS, Min SJ, Kim MJ, Kim JE, Kang TC. Leptomycin B ameliorates vasogenic edema formation induced by status epilepticus via inhibiting p38 MAPK/VEGF pathway. Brain Res. 2016 Nov 15;1651:27-35. doi: 10.1016/j.brainres.2016.09.023. Epub 2016 Sep 19. doi: 10.1016/j.vetpar.2015.12.034. Epub 2016 Jan 4. doi: 10.1155/2015/217304. Epub 2015 Apr 1.

合成参考文献


参考文献:10.1007/s00439-011-1058-x
摘要:Williamson SL, Giudici L, Kilstrup-Nielsen C, Gold W, Pelka GJ, Tam PP, Grimm A, Prodi D, Landsberger N, Christodoulou J. A novel transcript of cyclin-dependent kinase-like 5 (CDKL5) has an alternative C-terminus and is the predominant transcript in brain. Hum Genet. 2012 Feb;131(2):187–200. doi: 10.1007/s00439-011-1058-x.
参考文献:10.1007/s00430-011-0211-4
摘要:Cai M, Wang S, Long J, Zheng C. Probing of the nuclear import and export signals and subcellular transport mechanism of varicella-zoster virus tegument protein open reading frame 10. Medical Microbiology and Immunology. 2011 Jul 14;201(1):103–11. doi: 10.1007/s00430-011-0211-4.
参考文献:10.1186/1471-2407-11-294
摘要:Noske A, Schwabe M, Weichert W, Darb-Esfahani S, Buckendahl AC, Sehouli J, Braicu EI, Budczies J, Dietel M, Denkert C. An intracellular targeted antibody detects EGFR as an independent prognostic factor in ovarian carcinomas. BMC Cancer. 2011 Jul 14;11():294.
参考文献:10.1016/j.ijbiomac.2011.07.005
摘要:Anandharaj A, Yu J, Park W. Phosphorylation of threonine 190 is essential for nuclear localization and endocytosis of the FTS (Fused Toes Homolog) protein. International Journal of Biological Macromolecules. 2011 Nov;49(4):721–8. doi: 10.1016/j.ijbiomac.2011.07.005.
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