Vancomycin methyl ester

• 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: Vancomycin methyl ester
• 英文别名: methyl (1S,2R,18R,19R,22S,25R,28R,40S)-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylate
• 化学式: C₆₇H₇₇Cl₂N₉O₂₄
• 分子量: 1463.3
• InChiKey: DEHRLQFJHJGOCL-MOCCSWDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  102
• 可旋转键数：
  14
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  520
• 氢给体数：
  18
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  Vancomycin methyl ester 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 万古霉素
  参考文献：
  名称：

  Total Synthesis of Vancomycin—Part 4: Attachment of the Sugar Moieties and Completion of the Synthesis

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19990903)5:9<2648::aid-chem2648>3.0.co;2-q
• 作为产物：
  描述：

  盐酸万古霉素 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以32 mg的产率得到Vancomycin methyl ester
  参考文献：
  名称：

  Site-Selective Bromination of Vancomycin

  摘要：

  We report the site-selective bromination of vancomycin to produce, with substantial efficiency, previously unknown monobromovancomycins, a dibromovancomycin, and a tribromovancomycin. We document the inherent reactivity of native vancomycin toward N-bromophthalimide. We then demonstrate significant rate acceleration and perturbation of the inherent product distribution in the presence of a rationally designed peptide-based promoter. Alternative site selectivity is observed as a function of solvent and replacement of the peptide with guanidine.

  DOI：

  10.1021/ja301566t

文献信息

• Enzymatic Glycosylation of Vancomycin Aglycon: Completion of a Total Synthesis of Vancomycin and N- and C-Terminus Substituent Effects of the Aglycon Substrate
  作者：Atsushi Nakayama、Akinori Okano、Yiqing Feng、James C. Collins、Karen C. Collins、Christopher T. Walsh、Dale L. Boger

  DOI：10.1021/ol501568t

  日期：2014.7.3

  Studies on the further development of the sequential glycosylations of the vancomycin aglycon catalyzed by the glycosyltransferases GtfE and GtfD and the observation of unusual, perhaps unexpected, aglycon substrate substituent effects on the rate and efficiency of the initial glycosylation reaction are reported.

  报告了由糖基转移酶 GtfE 和 GtfD 催化的万古霉素苷元连续糖基化的进一步发展的研究，以及观察到不寻常的、也许是意想不到的苷元底物取代基对初始糖基化反应的速率和效率的影响。
• Total Synthesis of Vancomycin—Part 4: Attachment of the Sugar Moieties and Completion of the Synthesis
  作者：K. C. Nicolaou、Helen J. Mitchell、Nareshkumar F. Jain、Toshikazu Bando、Robert Hughes、Nicolas Winssinger、Swaminathan Natarajan、Alexandros E. Koumbis

  DOI：10.1002/(sici)1521-3765(19990903)5:9<2648::aid-chem2648>3.0.co;2-q

  日期：1999.9.3
• Site-Selective Bromination of Vancomycin
  作者：Tejas P. Pathak、Scott J. Miller

  DOI：10.1021/ja301566t

  日期：2012.4.11

  We report the site-selective bromination of vancomycin to produce, with substantial efficiency, previously unknown monobromovancomycins, a dibromovancomycin, and a tribromovancomycin. We document the inherent reactivity of native vancomycin toward N-bromophthalimide. We then demonstrate significant rate acceleration and perturbation of the inherent product distribution in the presence of a rationally designed peptide-based promoter. Alternative site selectivity is observed as a function of solvent and replacement of the peptide with guanidine.