6,9-Etheno-4,19-(iminomethano)-11,15:20,24-dimetheno-1H-10,2,18-benzoxadiazacyclohexacosine-carboxylic acid, 13-(4-((2R)-2-carboxy-2-(((phenylmethoxy)carbonyl)amino)ethyl)-2-chlorophenoxy)-8-chloro-16-(((1,1-dimethylethoxy)carbonyl)amino)-2,3,4,5,16,17,18,19-octahydro-5,12,23,25,27-pentahydroxy-3,17,30-trioxo-, 1-methyl ester, (1S,4S,5R,16R,19R)- | 164515-56-4

• 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: 6,9-Etheno-4,19-(iminomethano)-11,15:20,24-dimetheno-1H-10,2,18-benzoxadiazacyclohexacosine-carboxylic acid, 13-(4-((2R)-2-carboxy-2-(((phenylmethoxy)carbonyl)amino)ethyl)-2-chlorophenoxy)-8-chloro-16-(((1,1-dimethylethoxy)carbonyl)amino)-2,3,4,5,16,17,18,19-octahydro-5,12,23,25,27-pentahydroxy-3,17,30-trioxo-, 1-methyl ester, (1S,4S,5R,16R,19R)-
• 英文别名: (2R)-3-[3-chloro-4-[[(1R,13S,16S,17R,28R)-20-chloro-5,8,10,17,24-pentahydroxy-13-methoxycarbonyl-28-[(2-methylpropan-2-yl)oxycarbonylamino]-15,29,31-trioxo-22-oxa-14,30,32-triazahexacyclo[14.14.2.218,21.12,6.123,27.07,12]hexatriaconta-2(36),3,5,7(12),8,10,18,20,23,25,27(33),34-dodecaen-25-yl]oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 164515-56-4
• 化学式: C₅₆H₅₁Cl₂N₅O₁₈
• 分子量: 1152.95
• InChiKey: SGAOEMISANIUHU-ZBNITVSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  81
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  347
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  6,9-Etheno-4,19-(iminomethano)-11,15:20,24-dimetheno-1H-10,2,18-benzoxadiazacyclohexacosine-carboxylic acid, 13-(4-((2R)-2-carboxy-2-(((phenylmethoxy)carbonyl)amino)ethyl)-2-chlorophenoxy)-8-chloro-16-(((1,1-dimethylethoxy)carbonyl)amino)-2,3,4,5,16,17,18,19-octahydro-5,12,23,25,27-pentahydroxy-3,17,30-trioxo-, 1-methyl ester, (1S,4S,5R,16R,19R)- 在 三氟乙酸 作用下， 反应 0.25h， 以100%的产率得到Glycine, (2R)-2-(3-(4-((2R)-2-carboxy-2-(((phenylmethoxy)carbonyl)amino)ethyl)-2-chlorophenoxy)-4,5-dihydroxyphenyl)glycylglycyl-(betaR)-3-chloro-beta-hydroxy-L-tyrosyl-, 4-methyl ester, cyclic (15-34)-ether,cyclic 22,42-(4,6,6'-trihydroxy(1,1'-biphenyl)-3',2-diyl) deriv., (2(2R),4(2S))-
  参考文献：
  名称：

  Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 2. Deglucoteicoplanin-Derived Tetrapeptide

  摘要：

  The deglucoteicoplanin-derived tetrapeptide (TDTP), a key synthon suitable for the synthesis of modified glycopeptide antibiotics differing in the structure of the active site, was prepared from the product (RH-TD) of reductive hydrolysis of the 2,3-peptide bond of deglucoteicoplanin (TD) upon selective oxidation of the newly formed hydroxymethyl group and following simultaneous removal of amino acids 1 and 3 by double Edman degradation. The oxidation of the alcohol function of residue 2 in RH-TD was accomplished (Jones reagent) after protection of the two free amino groups as tert-butyl BOC carbamates and of most of phenolic hydroxy groups as benzyl CBZ carbonates. Esterification of the C-terminal carboxy group of intermediate di-BOC-RH-TD allowed the formation at the end of the process of the tetrapeptide (TDTP-Me) protected at one carboxy group as methyl ester. Selective protection of the primary N-4- and N-2-amino groups of TDTP-Me as BOC and CBZ carbamates, respectively, followed by removal of the BOC function, afforded a more suitable intermediate (N-2-CBZ-TDTP-Me) for the synthesis of new glycopeptides.

  DOI：

  10.1021/jo9506746
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 碳酸氢钠 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 9.08h， 生成 6,9-Etheno-4,19-(iminomethano)-11,15:20,24-dimetheno-1H-10,2,18-benzoxadiazacyclohexacosine-carboxylic acid, 13-(4-((2R)-2-carboxy-2-(((phenylmethoxy)carbonyl)amino)ethyl)-2-chlorophenoxy)-8-chloro-16-(((1,1-dimethylethoxy)carbonyl)amino)-2,3,4,5,16,17,18,19-octahydro-5,12,23,25,27-pentahydroxy-3,17,30-trioxo-, 1-methyl ester, (1S,4S,5R,16R,19R)-
  参考文献：
  名称：

  Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 2. Deglucoteicoplanin-Derived Tetrapeptide

  摘要：

  The deglucoteicoplanin-derived tetrapeptide (TDTP), a key synthon suitable for the synthesis of modified glycopeptide antibiotics differing in the structure of the active site, was prepared from the product (RH-TD) of reductive hydrolysis of the 2,3-peptide bond of deglucoteicoplanin (TD) upon selective oxidation of the newly formed hydroxymethyl group and following simultaneous removal of amino acids 1 and 3 by double Edman degradation. The oxidation of the alcohol function of residue 2 in RH-TD was accomplished (Jones reagent) after protection of the two free amino groups as tert-butyl BOC carbamates and of most of phenolic hydroxy groups as benzyl CBZ carbonates. Esterification of the C-terminal carboxy group of intermediate di-BOC-RH-TD allowed the formation at the end of the process of the tetrapeptide (TDTP-Me) protected at one carboxy group as methyl ester. Selective protection of the primary N-4- and N-2-amino groups of TDTP-Me as BOC and CBZ carbamates, respectively, followed by removal of the BOC function, afforded a more suitable intermediate (N-2-CBZ-TDTP-Me) for the synthesis of new glycopeptides.

  DOI：

  10.1021/jo9506746

文献信息

• Antiretroviral Activity of Semisynthetic Derivatives of Glycopeptide Antibiotics
  作者：Jan Balzarini、Christophe Pannecouque、Erik De Clercq、Andrey Y. Pavlov、Svetlana S. Printsevskaya、Olga V. Miroshnikova、Marina I. Reznikova、Maria N. Preobrazhenskaya

  DOI：10.1021/jm0300882

  日期：2003.6.1

  natural antibacterial glycopeptide antibiotics such as vancomycin, eremomycin, ristocetin A, teicoplanin A(2)-2, DA-40926, their aglycons, and also the products of their partial degradation with a destroyed or modified peptide core show marked anti-retroviral activity in cell culture. In particular, aglycon antibiotic derivatives containing various substituents of a preferably hydrophobic nature displayed

  多种天然抗菌糖肽抗生素的半合成衍生物，例如万古霉素，埃雷霉素，瑞斯托菌素A，替考拉宁A（2）-2，DA-40926，它们的糖苷配基，以及具有被破坏或修饰的肽核的部分降解产物在细胞培养中具有明显的抗逆转录病毒活性。尤其是，含有优选具有疏水性的各种取代基的糖苷配基抗生素衍生物在较低的微摩尔浓度下（50％抑制浓度）显示出对人类免疫缺陷病毒1型（HIV-1），HIV-2和莫洛尼鼠肉瘤病毒的活性（1-浓度范围为5 microM），而在250 microM或更高的浓度下不会对人淋巴细胞产生细胞抑制作用。抗生素糖苷配基衍生物的抗HIV作用方式可归因于病毒进入过程的抑制。
• Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 2. Deglucoteicoplanin-Derived Tetrapeptide
  作者：Adriano Malabarba、Romeo Ciabatti、Michele Maggini、Pietro Ferrari、Luigi Colombo、Maurizio Denaro

  DOI：10.1021/jo9506746

  日期：1996.1.1

  The deglucoteicoplanin-derived tetrapeptide (TDTP), a key synthon suitable for the synthesis of modified glycopeptide antibiotics differing in the structure of the active site, was prepared from the product (RH-TD) of reductive hydrolysis of the 2,3-peptide bond of deglucoteicoplanin (TD) upon selective oxidation of the newly formed hydroxymethyl group and following simultaneous removal of amino acids 1 and 3 by double Edman degradation. The oxidation of the alcohol function of residue 2 in RH-TD was accomplished (Jones reagent) after protection of the two free amino groups as tert-butyl BOC carbamates and of most of phenolic hydroxy groups as benzyl CBZ carbonates. Esterification of the C-terminal carboxy group of intermediate di-BOC-RH-TD allowed the formation at the end of the process of the tetrapeptide (TDTP-Me) protected at one carboxy group as methyl ester. Selective protection of the primary N-4- and N-2-amino groups of TDTP-Me as BOC and CBZ carbamates, respectively, followed by removal of the BOC function, afforded a more suitable intermediate (N-2-CBZ-TDTP-Me) for the synthesis of new glycopeptides.