(1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-15-borono-2,18,32,35,37,48-hexahydroxy-19-[[(2R)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]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(50),4,6(49),8(48),9,11,14,16,29(45),30,32,34(39),35,37,46-pentadecaene-40-carboxylic acid | 1433954-87-0

• 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: (1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-15-borono-2,18,32,35,37,48-hexahydroxy-19-[[(2R)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]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(50),4,6(49),8(48),9,11,14,16,29(45),30,32,34(39),35,37,46-pentadecaene-40-carboxylic acid
• CAS: 1433954-87-0
• 化学式: C₅₈H₆₃BN₈O₂₁
• 分子量: 1218.99
• InChiKey: XNJIEUBENKEIIF-WEFWLKFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  88
• 可旋转键数：
  11
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  465
• 氢给体数：
  16
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  (1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-15-borono-2,18,32,35,37,48-hexahydroxy-19-[[(2R)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]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(50),4,6(49),8(48),9,11,14,16,29(45),30,32,34(39),35,37,46-pentadecaene-40-carboxylic acid 在 copper dichloride 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Investigation into the functional impact of the vancomycin C-ring aryl chloride

  摘要：

  A vancomycin aglycon analogue that possesses a reduced C-ring and an intact E-ring chloride was prepared and its antimicrobial activity towards Staphylococcus aureus and binding affinity to model cell wall ligands were established. Comparison of the derivative with a series of vancomycin aglycon analogues that possess and lack the chloro substituents on the aryl C- and E-rings defines the impact and further refines the role the C-ring chloride plays in promoting both target binding affinity and binding selectivity for D-Ala-D-Ala and its impact on antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.080
• 作为产物：
  描述：

  四羟基二硼 、 (1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37,48-hexahydroxy-19-[[(2R)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]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-carboxylic acid 在 XPhos Pd G2 、 dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-3-yl)phosphine 、 potassium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以19%的产率得到(1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-15-borono-2,18,32,35,37,48-hexahydroxy-19-[[(2R)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]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(50),4,6(49),8(48),9,11,14,16,29(45),30,32,34(39),35,37,46-pentadecaene-40-carboxylic acid
  参考文献：
  名称：

  Investigation into the functional impact of the vancomycin C-ring aryl chloride

  摘要：

  A vancomycin aglycon analogue that possesses a reduced C-ring and an intact E-ring chloride was prepared and its antimicrobial activity towards Staphylococcus aureus and binding affinity to model cell wall ligands were established. Comparison of the derivative with a series of vancomycin aglycon analogues that possess and lack the chloro substituents on the aryl C- and E-rings defines the impact and further refines the role the C-ring chloride plays in promoting both target binding affinity and binding selectivity for D-Ala-D-Ala and its impact on antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.080

文献信息

• Probing the Role of the Vancomycin E-Ring Aryl Chloride: Selective Divergent Synthesis and Evaluation of Alternatively Substituted E-Ring Analogues
  作者：Joseph R. Pinchman、Dale L. Boger

  DOI：10.1021/jm4004494

  日期：2013.5.23

  The selective functionalization of vancomycin aglycon derivatives through conversion of the E-ring aryl chloride to a reactive boronic acid and its use in the synthesis of a systematic series of vancomycin E-ring analogues are described. The series was used to examine the E-ring chloride impact in binding D-Ala-D-Ala and on antimicrobial activity. In contrast to the reduced activity of the unsubstituted E-ring derivatives, hydrophobic and relatively nonpolar substituents approach or match the chloro-substituted vancomycin and were insensitive to the electronic character of the substituent (e.g., Cl vs CN/OMe), whereas highly polar substituents fail to provide the enhancements. Moreover, the active permethylated vancomycin aglycon derivatives exhibit VanB VRE antimicrobial activity at levels that approach (typically within 2-fold) their activity against sensitive bacteria. The robust borylation reaction also enabled the functionalization of a minimally protected vancomycin aglycon (N-Boc-vancomycin aglycon) and provides a direct method for the preparation of previously inaccessible analogues.
• Investigation into the functional impact of the vancomycin C-ring aryl chloride
  作者：Joseph R. Pinchman、Dale L. Boger

  DOI：10.1016/j.bmcl.2013.06.080

  日期：2013.9

  A vancomycin aglycon analogue that possesses a reduced C-ring and an intact E-ring chloride was prepared and its antimicrobial activity towards Staphylococcus aureus and binding affinity to model cell wall ligands were established. Comparison of the derivative with a series of vancomycin aglycon analogues that possess and lack the chloro substituents on the aryl C- and E-rings defines the impact and further refines the role the C-ring chloride plays in promoting both target binding affinity and binding selectivity for D-Ala-D-Ala and its impact on antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.