CAS: 2825-00-5; Aureothin

该化合物是属于被称为聚氯酸酯的化合物类别的天然产品,主要由真菌的某些物种* Penicillium* 生产,并展示了各种生物活动,包括抗微生物和抗风素特性.Aureothin的特征是其复杂的分子结构,包括多个环和功能组,有助于其反应和生物功效.该化合物因其在治疗各种感染和疾病方面的潜在应用而引起了对药物研究的兴趣.此外,该化合物独特的化学特性使它成为天然产品化学领域研究的课题.与许多自然化合物一样,提取和净化过程具有挑战性,并且持续研究的目的是探索其行动和潜在治疗用途的机制.

结构式图片

物理性质

MSDS等安全信息

合成工艺路线路线简述

    📜(R)-2-((3E,5E)-1-Hydroxy-3,5-Dimethyl-6-(4-Nitrophenyl)Hexa-3,5-Dienyl)-6-Methoxy-3,5-Dimethyl-4H-Pyran-4-One置于nadph,Glucose-6-Phosphate,Bakers' Yeast Glucose-6-Phosphate Dehydrogenase,Cytochrome P450 Monooxygenase Aurh,Spinach Ferredoxin-Nadp-Oxidoreductase,三羟甲基氨基甲烷,Spinach Ferredoxin体系中,用 水 用作溶剂,化学反应生成金链菌素
    参考文献:单个细胞色素p450单加氧酶(aurh)催化的顺序不对称聚酮化合物杂环化.
    标题:单个细胞色素p450单加氧酶(aurh)催化的顺序不对称聚酮化合物杂环化.
    摘要:
    Doi:10.1002/anie.200803714

    海关参考信息

    专利信息


    专利号:US-10655153-B2
    优先权日:2017-03-14
    标 题 :Chemoenzymatic synthesis of peptide beta-lactones and beta-hydroxy acids
    发明人：WENCEWICZ TIMOTHY A; SCHAFFER JASON E; RECK MARGARET R
    权利人:WENCEWICZ TIMOTHY A; SCHAFFER JASON E; RECK MARGARET R; UNIV WASHINGTON
    摘要:Methods of producing peptide beta-lactones and beta-hydroxy acids are disclosed that include contacting a beta-hydroxy-alpha-amino acid, an aryl carrier protein (ObiD), and ATP with a non-ribosomal protein synthetase. A continuous flow reactor is disclosed that includes an elongate conduit with at least one region that includes a first region with a non-ribosomal protein synthetase immobilized to a substrate. The non-ribosomal protein synthetase of the continuous flow reactor is configured to contact a flow of a reaction mixture that includes a beta-hydroxy-alpha-amino acid and an aryl carrier protein. The non-ribosomal protein synthetase is further configured to release a peptide beta-lactone into the flow of the reaction mixture.

    专利号:US-2018265905-A1
    优先权日:2017-03-14
    标 题:Chemoenzymatic synthesis of peptide beta-lactones and beta-hydroxy acids

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    主要参考文献


    1: Drissya T, Induja DK, Poornima MS, Jesmina ARS, Prabha B, Saumini M, Suresh CH, Raghu KG, Kumar BSD, Lankalapalli RS. A novel aureothin diepoxide derivative from Streptomyces sp. NIIST-D31 strain. J Antibiot (Tokyo). 2022 Sep;75(9):491-497. doi: 10.1038/s41429-022-00547-1. Epub 2022 Aug 4. 70(15-16):1833-40. doi: 10.1016/j.phytochem.2009.05.022. Epub 2009 Aug 3. 81(12):5190-201. doi: 10.1021/acs.joc.6b00878. Epub 2016 May 27. 70(36):11274-11280. doi: 10.1021/acs.jafc.2c03537. Epub 2022 Aug 30. 12(1):3947. doi: 10.1038/s41598-022-07879-w.
    6: Ueda JY, Hashimoto J, Nagai A, Nakashima T, Komaki H, Anzai K, Harayama S, Doi T, Takahashi T, Nagasawa K, Natsume T, Takagi M, Shin-ya K. New aureothin derivative, alloaureothin, from Streptomyces sp. MM23. J Antibiot (Tokyo). 2007 May;60(5):321-4. doi: 10.1038/ja.2007.41. 10(1):3918. doi: 10.1038/s41467-019-11896-1.
    8: Busch B, Ueberschaar N, Sugimoto Y, Hertweck C. Interchenar retrotransfer of aureothin intermediates in an iterative polyketide synthase module. J Am Chem Soc. 2012 Aug 1;134(30):12382-5. doi: 10.1021/ja304454r. Epub 2012 Jul 23. 10(1):1326. doi: 10.1038/s41598-020-57843-9.

    合成参考文献


    摘要:Negishi, E.; Wang, G., Science of Synthesis, (2009) 46, 290.
    摘要:WASHIZU F, UMEZAWA H, SUGIYAMA N. Chemical studies on a toxic product of Streptomyces thioluteus, aureothin. J Antibiot (Tokyo). 1954 Mar;7(2):60.
    参考文献:10.1016/j.chembiol.2003.11.009
    摘要:He J, Hertweck C. Iteration as programmed event during polyketide assembly; molecular analysis of the aureothin biosynthesis gene cluster. Chem Biol. 2003 Dec;10(12):1225–32. doi: 10.1016/j.chembiol.2003.11.009.
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