mannopeptimycin-α

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: mannopeptimycin-α
• 英文别名: (3S,6R,9S,12R,15S)-9-[(R)-[(4S)-2-amino-4,5-dihydro-1H-imidazol-4-yl]-hydroxymethyl]-6-[(R)-[(4S)-2-amino-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4,5-dihydroimidazol-4-yl]-hydroxymethyl]-12-[[4-[(2R,3S,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]methyl]-3-(hydroxymethyl)-15-[(1S)-1-phenylethyl]-1,4,7,10,13,16-hexazacyclooctadecane-2,5,8,11,14,17-hexone
• 化学式: C₅₄H₇₈N₁₂O₂₅
• 分子量: 1295.28
• InChiKey: NDAFEWFOUCZEQM-YFFHIAQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  91
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  596
• 氢给体数：
  23
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  mannopeptimycin-α 在 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 作用下， 生成
  参考文献：
  名称：

  甘露肽霉素糖肽抗生素的醚和卤代衍生物的合成和评价。

  摘要：

  合成了许多具有不同空间体积和亲脂性的甘露肽霉素-α的6-O-醚和4-O-醚衍生物用于结构-活性关系研究。还制备了新的碘和溴甘露肽霉素-α。这些化合物是通过亲电芳族取代合成的。许多新的醚衍生物对革兰氏阳性耐药菌株（包括VRE，MRSA和PRSP）表现出有效的抗菌活性。

  DOI：

  10.1016/s0960-894x(03)00542-0

文献信息

• Novel ether derivatives of mannopeptimycin glycopeptide antibiotic
  作者：Phaik-Eng Sum、David How、Nancy Torres、Peter J Petersen、Eileen B Lenoy、William J Weiss、Tarek S Mansour

  DOI：10.1016/s0960-894x(03)00045-3

  日期：2003.3

  Novel ether derivatives of mannopeptimycin glycopeptide were synthesized to probe their SAR. Many of these derivatives exhibited potent antibacterial activity against methicillin resistant and vancomycin resistant strains. These ether derivatives were prepared via reductive ring cleavage of acetals to give a mixture of 6-O, 4-O, 3-O, and 2-O-ether isomers. Both 6-O-ether and 4-O-ether showed significantly enhanced antibacterial activity over the parent and the isovalerate esters. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Mannopeptimycin esters and carbonates, potent antibiotic agents against drug-resistant bacteria
  作者：Haiyin He、Bo Shen、Peter J. Petersen、William J. Weiss、Hui Y. Yang、Ting-Zhong Wang、Russell G. Dushin、Frank E. Koehn、Guy T. Carter

  DOI：10.1016/j.bmcl.2003.09.071

  日期：2004.1

  A series of ester and carbonate derivatives of the glycopeptide mannopeptimycin alpha (1) with potent activity against G(+) bacteria, including the methicillin-resistant staphylococci and vancomycin-resistant enterococci, was synthesized. The SAR data obtained from natural and semisynthetic compounds demonstrated the importance of a hydrophobic group in the terminal mannosyl moiety for antibacterial activity. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of ether and halogenated derivatives of mannopeptimycin glycopeptide antibiotics
  作者：Phaik-Eng Sum、David How、Nancy Torres、Peter J. Petersen、Joseph Ashcroft、Edmund I. Graziani、Frank E. Koehn、Tarek S. Mansour

  DOI：10.1016/s0960-894x(03)00542-0

  日期：2003.8

  A number of 6-O-ether and 4-O-ether derivatives of mannopeptimycin-alpha with different steric bulk and lipophilicity were synthesized for structure-activity relationship study. Novel iodo and bromo mannopeptimycin-alpha were also prepared. These compounds were synthesized via electrophilic aromatic substitution. Many of the new ether derivatives exhibited potent antibacterial activity against Gram-positive

  合成了许多具有不同空间体积和亲脂性的甘露肽霉素-α的6-O-醚和4-O-醚衍生物用于结构-活性关系研究。还制备了新的碘和溴甘露肽霉素-α。这些化合物是通过亲电芳族取代合成的。许多新的醚衍生物对革兰氏阳性耐药菌株（包括VRE，MRSA和PRSP）表现出有效的抗菌活性。