marthiapeptide A | 1412945-69-7

• 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: marthiapeptide A
• 英文别名: Marthiapeptide A；(13R,16R,19S,22R)-16-benzyl-19-[(2S)-butan-2-yl]-22-methyl-3,7,11,24-tetrathia-15,18,21,26,27,28,29-heptazapentacyclo[21.2.1.12,5.16,9.110,13]nonacosa-1(25),2(29),4,6(28),8,10(27),23(26)-heptaene-14,17,20-trione
• CAS: 1412945-69-7
• 化学式: C₃₀H₃₁N₇O₃S₄
• 分子量: 665.885
• InChiKey: BTQRWSUKDHTMKD-DUKGZVIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  248
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  marthiapeptide A 在 盐酸 、 水 作用下， 反应 18.0h， 生成 L-异亮氨酸
  参考文献：
  名称：

  Marthiapeptide A, an Anti-infective and Cytotoxic Polythiazole Cyclopeptide from a 60 L Scale Fermentation of the Deep Sea-Derived Marinactinospora thermotolerans SCSIO 00652

  摘要：

  A new sequential tristhiazole-thiazoline-containing cyclic peptide, marthiapeptide A (1), was isolated from a 60 L scale culture of the deep South China Sea-derived strain Marinactinospora thermotolerans SCSIO 00652. The planar structure and absolute configuration of 1 were elucidated by application of spectroscopic techniques, as well as by single-crystal X-ray diffraction and chiral-phase HPLC analysis of the acid hydrolysates. Marthiapeptide A (1) exhibited antibacterial activity against a panel of Gram-positive bacteria, with MIC values ranging from 2.0 to 8.0 mu g/mL, and displayed strong cytotoxic activity against a panel of human cancer cell lines with IC50 values ranging from 0.38 to 0.52 mu M.

  DOI：

  10.1021/np300554f
• 作为产物：
  描述：

  Boc-D-苯丙氨酸 在 ammonium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 lithium hydroxide monohydrate 、 水 、 碳酸氢钠 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.08h， 生成 marthiapeptide A
  参考文献：
  名称：

  Synthesis of the Natural Product Marthiapeptide A

  摘要：

  The first total synthesis of marthiapeptide A is reported. Two synthetic procedures are described: the first, which was unsuccessful, attempts to close the ring at position I, and the second, which was successful, closes the ring at position II. It appears that the first route was unsuccessful because it required cyclization next to the rigid thiazole moiety, whereas the second route closed next to the more flexible thiazoline ring.

  DOI：

  10.1021/acs.orglett.5b02574

文献信息

• [EN] ANTIBIOTIC TETRATHIAZOMYCIN A AND PREPARATION METHOD THEREOF AND USE IN PREPARATION OF ANTITUMOUR DRUG<br/>[FR] TÉTRATHIAZOMYCINE A, UN ANTIBIOTIQUE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION DANS LE CADRE DE LA PRÉPARATION DE MÉDICAMENTS ANTI-TUMORAUX
  申请人：SOUTH CHINA SEA INST OCEANOLOG

  公开号：WO2014005408A1

  公开（公告）日：2014-01-09

  本发明提供抗生素Tetrathiazomycin A及其制备方法和在制备抗肿瘤药物中的应用。Tetrathiazomycin A其结构式如式（I）所示。本发明从放线菌属Marinactinospora thermotolerans SCSIO 00652的发酵培养物中分离得到新的具有抗肿瘤活性的化合物Tetrathiazomycin A，为化合物Tetrathiazomycin A的制备开辟了新的途径，并且本发明的化合物Tetrathiazomycin A具有较好的抗肿瘤活性，能应用制备抗肿瘤药物中，为抗肿瘤药物的开发提供了先导化合物。
• Synthesis of the Natural Product Marthiapeptide A
  作者：Yuqi Zhang、Md. Amirul Islam、Shelli R. McAlpine

  DOI：10.1021/acs.orglett.5b02574

  日期：2015.11.6

  The first total synthesis of marthiapeptide A is reported. Two synthetic procedures are described: the first, which was unsuccessful, attempts to close the ring at position I, and the second, which was successful, closes the ring at position II. It appears that the first route was unsuccessful because it required cyclization next to the rigid thiazole moiety, whereas the second route closed next to the more flexible thiazoline ring.
• Marthiapeptide A, an Anti-infective and Cytotoxic Polythiazole Cyclopeptide from a 60 L Scale Fermentation of the Deep Sea-Derived <i>Marinactinospora thermotolerans</i> SCSIO 00652
  作者：Xiao Zhou、Hongbo Huang、Yuchan Chen、Jiaheng Tan、Yongxiang Song、Jianhua Zou、Xinpeng Tian、Yan Hua、Jianhua Ju

  DOI：10.1021/np300554f

  日期：2012.12.28

  A new sequential tristhiazole-thiazoline-containing cyclic peptide, marthiapeptide A (1), was isolated from a 60 L scale culture of the deep South China Sea-derived strain Marinactinospora thermotolerans SCSIO 00652. The planar structure and absolute configuration of 1 were elucidated by application of spectroscopic techniques, as well as by single-crystal X-ray diffraction and chiral-phase HPLC analysis of the acid hydrolysates. Marthiapeptide A (1) exhibited antibacterial activity against a panel of Gram-positive bacteria, with MIC values ranging from 2.0 to 8.0 mu g/mL, and displayed strong cytotoxic activity against a panel of human cancer cell lines with IC50 values ranging from 0.38 to 0.52 mu M.