CAS: 33404-78-3; Negamycin

该化合物是一个复杂的有机化合物,其独特的结构特征包括多个氨基氨基组和氢氮功能组,该化合物是碳二酸的衍生物,有助于其生物活动和药用化学的潜在应用.氨基酸组的存在表明,它可能参与各种生物化学反应,有可能成为更复杂的分子的构件或协调化学的离心体. 碳箱甲基和甲基氢二氟氮基次组增强它的溶性性和再活动性,使之适合各种合成途径.此外,"L-threo"称的立体化学学表明,它有可能会影响其与生物系统互动的具体空间安排.

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物理性质

MSDS等安全信息

    合成工艺路线路线简述

      📜(R)-5-{(R)-2-[benzyl-((R)-1-Phenyl-Ethyl)-Amino]-3-Carboxy-Propyl}-2,2-Dimethyl-Oxazolidine-3-Carboxylic Acid Tert-Butyl Ester置于20 % Pd(Oh)2/c,氢气,1-羟基苯并三唑,溶剂黄146,三乙胺,N,N'-二环己基碳二亚胺,三氟乙酸体系中,用 甲醇,二氯甲烷 用作溶剂,20.0 °C,506.66 Kpa 条件下,反应 43.75H,反应生成2-[[(3,6-二氨基-5-羟基己烷酰基)氨基]-甲基氨基]乙酸
      参考文献:通过锂酰胺共轭物加成(+)-新霉素,(+)-3-表-新霉素和斯培比林c的不对称合成
      标题:通过锂酰胺共轭物加成(+)-新霉素,(+)-3-表-新霉素和斯培比林c的不对称合成
      摘要:4-氯乙酰乙酸乙酯的化学和对映选择性还原以及对映纯n-苄基-N-(α-甲基苄基)酰胺对映体选择性共轭加成到α,β-不饱和酯中已被用作总不对称反应的关键步骤(+)的合成-Negamycin(在13个步骤和24%的总收率),(+)-3-外延-Negamycin(在13个步骤和10%的总产率)和sperabillin C(在17个步骤,13%总收率)从可商购的原料中提取.
      Doi:10.1016/j.Tet.2010.10.067

      海关参考信息

      专利信息


      专利号:EP-0229313-B1
      优先权日:1985-12-27
      标 题:Compound related to antibiotic tan-749 and their production
      摘要:The compound of the formula wherein R<1> is hydrogen, hexanoyl, or sorbyl, R<2> is hydrogen or methyl, R<3> is an amino which may optionally be protected, and R<4> is hydroxyl or 2-amidino-ethylamino, with the proviso that when both R<1> and R<2> are hydrogen and R<3> is amino, R<4> is 2-amidino-ethylamino, or when R<1> is sorbyl and R<4> is 2-amidino-ethylamino, R<3> is a protected amino, or salts thereof can work well as the intermediate material for the synthesis of TAN-749, an antibiotic which is useful as a therapeutic drug for bacterial infectious diseases.

      专利号:CN-107129440-B
      优先权日:2017-06-20
      标题:A kind of total synthesis method of natural product (+)-negamycin

      专利号:CN-107129440-A
      优先权日:2017-06-20
      标 题 :A kind of total synthesis method of natural product (+)-negamycin

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      主要参考文献


      1: Pranke I, Bidou L, Martin N, Blanchet S, Hatton A, Karri S, Cornu D, Costes B, Chevalier B, Tondelier D, Girodon E, Coupet M, Edelman A, Fanen P, Namy O, Sermet-Gaudelus I, Hinzpeter A. Factors influencing readthrough therapy for frequent cystic fibrosis premature termination codons. ERJ Open Res. 2018 Feb 23;4(1). pii: 00080-2017. doi: 10.1183/23120541.00080-2017. eCollection 2018 Jan.
      2: Taguchi A, Hamada K, Shiozuka M, Kobayashi M, Murakami S, Takayama K, Taniguchi A, Usui T, Matsuda R, Hayashi Y. Structure-Activity Relationship Study of Leucyl-3-epi-deoxynegamycin for Potent Premature Termination Codon Readthrough. ACS Med Chem Lett. 2017 Sep 29;8(10):1060-1065. doi: 10.1021/acsmedchemlett.7b00269. eCollection 2017 Oct 12.
      3: Taguchi A, Hamada K, Hayashi Y. Chemotherapeutics overcoming nonsense mutation-associated genetic diseases: medicinal chemistry of negamycin. J Antibiot (Tokyo). 2018 Feb;71(2):205-214. doi: 10.1038/ja.2017.112. Epub 2017 Sep 27. Review. doi: 10.1073/pnas.1605127113. Epub 2016 Jul 5.

      合成参考文献


      摘要:Journal of Antibiotics., 23(170), 1970 []
      参考文献:10.1016/j.bmcl.2004.04.036|10.1016/s0960-894x(04)00539-6
      摘要:Raju B, Anandan S, Gu S, Herradura P, O’Dowd H, Kim B, Gomez M, Hackbarth C, Wu C, Wang W, Yuan Z, White R, Trias J, Patel DV. Conformationally restricted analogs of deoxynegamycin. Bioorganic & Medicinal Chemistry Letters. 2004 Jun;14(12):3103–7. doi: 10.1016/j.bmcl.2004.04.036.
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