gentamicin C2 | 287916-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: gentamicin C2
• 英文别名: gentamicin C2,C2a；gentamycin C2；gentamycin 3；gentamycin C2 + C2a；gentamicin 3；gentamicin C_1A；gentamicin C2a；(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• CAS: 287916-51-2
• 化学式: C₂₀H₄₁N₅O₇
• 分子量: 463.575
• InChiKey: XUFIWSHGXVLULG-IBLUXPFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  214
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-硝基糠醛 、 gentamicin C2 以 乙醇 为溶剂， 生成 1L-O⁴-[4-methyl-3-methylamino-N,O⁴-((Ξ)-5-nitro-furan-2-ylmethanediyl)-β-L-3-deoxy-arabinopyranosyl]-N,N'-bis-(5-nitro-furan-2-ylmethylene)-O⁶-{(2R)-3c-(5-nitro-furan-2-ylmethyleneamino)-6t-[(Ξ)-1-(5-nitro-furan-2-ylmethyleneamino)-ethyl]-tetrahydro-pyran-2r-yl}-2-deoxy-streptamine
  参考文献：
  名称：

  庆大霉素抗生素。4.庆大霉素C2与芳香族和脂肪族醛的缩合产物。

  摘要：

  DOI：

  10.1021/jm00293a026
• 作为试剂：
  描述：

  庆大霉素 在 gentamicin C₁ 、 gentamicin C2 、 triflic azide 、 copper(II) sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 以55%的产率得到
  参考文献：
  名称：

  Structure–toxicity relationship of aminoglycosides: Correlation of 2′-amine basicity with acute toxicity in pseudo-disaccharide scaffolds

  摘要：

  A new pseudo-disaccharide NB23 with a 3',4'-methylidene protection was designed and its properties were evaluated in comparison to other two structurally related pseudo-disaccharides. The basicity of the 2'-amine was found to be well correlated to acute toxicity data in mice: the increase in the basicity is associated with the toxicity increase. Based on these data, a new pseudo-trisaccharide NB45 was constructed. NB45 exhibited significant antibacterial activity while at the same time retained low acute toxicity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.053

文献信息

• [EN] ANIONIC CONJUGATES OF GLYCOSYLATED BACTERIAL METABOLITE<br/>[FR] CONJUGUÉS ANIONIQUES D'UN MÉTABOLITE BACTÉRIEN GLYCOSYLÉ
  申请人：GLYCAN BIOSCIENCES PTY LTD

  公开号：WO2010037179A1

  公开（公告）日：2010-04-08

  The invention relates to anionic conjugates of glycosylated bacterial metabolites that may be used to mimic the structure and/or activity of the anionic bioactive molecules known as glycosaminoglycans (GAGs). The invention also relates to processes for the preparation of the conjugates. Such conjugates are useful in the prophylaxis and/or treatment of disease conditions and in particular chronic disease conditions such as inflammatory (including allergic) diseases, metastatic cancers and infection by pathogenic agents including bacteria, viruses or parasites.

  该发明涉及与糖基化细菌代谢产物的阴离子结合物，可用于模拟被称为糖胺聚糖（GAGs）的阴离子生物活性分子的结构和/或活性。该发明还涉及制备这些结合物的过程。这些结合物在预防和/或治疗疾病条件方面具有用处，特别是慢性疾病条件，如炎症（包括过敏）疾病、转移性癌症和感染病原体（包括细菌、病毒或寄生虫）的情况。
• Novel aminoglycosides and uses thereof in the treatment of genetic disorders
  申请人：Bassov Timor

  公开号：US20090093418A1

  公开（公告）日：2009-04-09

  A new class of paromomycin-derived aminoglycosides, which exhibit efficient stop-codon mutation suppression activity, low toxicity and high selectivity towards eukaryotic cells are provided. Also provided are chemical and chemo-enzymatic processes of preparing these paromomycin-derived aminoglycosides and intermediates thereof, as well as pharmaceutical compositions containing the same, and uses thereof in the treatment of genetic disorders.

  提供了一类新型的巴罗霉素衍生氨基糖苷类化合物，具有高效的终止密码子突变抑制活性、低毒性和高选择性作用于真核细胞。同时提供了制备这些巴罗霉素衍生氨基糖苷类化合物及其中间体的化学和化酶过程，以及含有它们的药物组合物，并在遗传疾病治疗中的应用。
• Site-specific aminoglycoside derivatives and their use in immunodiagnostic assays
  申请人：——

  公开号：US20030060430A1

  公开（公告）日：2003-03-27

  A method of making a derivatized aminoglycoside includes reacting an aminoglycoside with at least 2 equivalents of a divalent metal ion in an aprotic solvent to complex two neighboring amino group and hydroxyl group pairs; reacting the non-complexed amino groups with a protecting reagent to provide protecting groups; removing the divalent metal ion to provide two unprotected amino groups; reacting one of the unprotected amino groups with a reactive substance containing an linker, a carrier, or a label; and removing the protecting groups. This method can be used to produce novel compounds and reagents.

  制备衍生氨基糖苷的方法包括在无极性溶剂中将氨基糖苷与至少2当量的二价金属离子反应，以形成两个相邻氨基和羟基对的络合物；将未形成络合物的氨基基团与保护试剂反应以提供保护基团；去除二价金属离子以提供两个未受保护的氨基基团；将其中一个未受保护的氨基基团与含有连接剂、载体或标记的反应物质反应；最后去除保护基团。这种方法可以用来生产新颖的化合物和试剂。
• Aminoglycoside-polyamine displacers and methods of use in displacement chromatography
  申请人：Rege Kaushal

  公开号：US20070049741A1

  公开（公告）日：2007-03-01

  Aminoglycoside-polyamines are disclosed along with methods of use thereof in displacement chromatography and as DNA-binding ligands. The aminoglycoside-polyamines are derivatives of carbohydrates, such as sugars, amino sugars, deoxysugars, glycosides, nucleosides and their substituted counterparts. The subject polyamines possess a group in place of at least one hydrogen atom of at least one hydroxyl group of the carbohydrate compound. In these compounds R 1 is an alkyl group or an azaalkyl group, and R 2 is a primary or secondary amino group.

  本文披露了氨基糖苷-多胺以及它们在置换色谱和作为DNA结合配体中的使用方法。氨基糖苷-多胺是碳水化合物的衍生物，例如糖，氨基糖，去氧糖，糖苷，核苷和它们的取代物。这些多胺具有取代至少一种碳水化合物化合物的至少一个羟基的氨基团。在这些化合物中，R1是烷基或氮杂基，R2是一级或二级氨基。
• Site-specific aminoglycoside derivatives for use in immunodiagnostic assays
  申请人：——

  公开号：US20040138425A1

  公开（公告）日：2004-07-15

  A method of making a derivatized aminoglycoside includes reacting an aminoglycoside with at least 2 equivalents of a divalent metal ion in an aprotic solvent to complex two neighboring amino group and hydroxyl group pairs; reacting the non-complexed amino groups with a protecting reagent to provide protecting groups; removing the divalent metal ion to provide two unprotected amino groups; reacting one of the unprotected amino groups with a reactive substance containing an linker, a carrier, or a label; and removing the protecting groups. This method can be used to produce novel compounds and reagents.

  一种制备衍生氨基糖苷的方法，包括在无质子溶剂中将氨基糖苷与至少2当量的二价金属离子反应，形成两个相邻氨基和羟基对的络合物；将未络合的氨基基团与保护试剂反应，提供保护基；去除二价金属离子，得到两个未保护的氨基基团；将其中一个未保护的氨基基团与含有连接剂、载体或标记的反应性物质反应；去除保护基。该方法可用于生产新的化合物和试剂。