N-(3-amino-3-oxoprop-1-en-2-yl)-2-[(1R,8S,11Z,15S,18S,25S,26R,35R,37S,40S,46S,53S,59S)-37-[(2S)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-31-[(1S)-1-hydroxyethyl]-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide | 1157858-07-5

• 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: N-(3-amino-3-oxoprop-1-en-2-yl)-2-[(1R,8S,11Z,15S,18S,25S,26R,35R,37S,40S,46S,53S,59S)-37-[(2S)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-31-[(1S)-1-hydroxyethyl]-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide
• CAS: 1157858-07-5
• 化学式: C₆₉H₈₂N₁₈O₁₇S₅
• 分子量: 1595.85
• InChiKey: XORNKFRBKXGWND-WYXFJBRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  109
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  672
• 氢给体数：
  16
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-(3-amino-3-oxoprop-1-en-2-yl)-2-[(1R,8S,11Z,15S,18S,25S,26R,35R,37S,40S,46S,53S,59S)-37-[(2S)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-31-[(1S)-1-hydroxyethyl]-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以6.6 mg的产率得到
  参考文献：
  名称：

  d-Cysteine occurrence in thiostrepton may not necessitate an epimerase

  摘要：

  研究表明，天然产品硫肽抗生素硫司肽在其噻唑啉残基上发生了简单的表聚作用，而自然观察到的 D-构型则发生了简单的表聚作用，这表明经典的表聚酶可能没有参与其生物合成。

  DOI：

  10.1039/b912733j
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到N-(3-amino-3-oxoprop-1-en-2-yl)-2-[(1R,8S,11Z,15S,18S,25S,26R,35R,37S,40S,46S,53S,59S)-37-[(2S)-butan-2-yl]-18-[(2S,3R)-2,3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-31-[(1S)-1-hydroxyethyl]-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecazanonacyclo[23.23.9.329,35.12,5.112,15.119,22.154,57.01,53.032,60]tetrahexaconta-2(64),4,12(63),19(62),21,29(61),30,32(60),33,51,54,57-dodecaen-51-yl]-1,3-thiazole-4-carboxamide
  参考文献：
  名称：

  d-Cysteine occurrence in thiostrepton may not necessitate an epimerase

  摘要：

  研究表明，天然产品硫肽抗生素硫司肽在其噻唑啉残基上发生了简单的表聚作用，而自然观察到的 D-构型则发生了简单的表聚作用，这表明经典的表聚酶可能没有参与其生物合成。

  DOI：

  10.1039/b912733j

文献信息

• Targeted Isolation of Saalfelduracin B–D from <i>Amycolatopsis saalfeldensis</i> Using LC-MS/MS-Based Molecular Networking
  作者：Soohyun Um、Elena Seibel、Felix Schalk、Sven Balluff、Christine Beemelmanns

  DOI：10.1021/acs.jnatprod.0c01027

  日期：2021.4.23

  High-resolution tandem mass spectrometry (HR-MS2)-based metabolomic studies of Amycolatopsis saalfeldensis, isolated from the “Saalfelder Feengrotten” caves in Germany, led to the isolation of three ribosomally synthesized and post-translationally modified type II thiopeptides, saalfelduracin B–D (1–3) and the known saalfelduracin A (4). The structures of all four compounds were determined by comparative

  从德国的“Saalfelder Feengrotten”洞穴中分离出的Amycolatopsis saalfeldensis基于高分辨率串联质谱 (HR-MS 2 ) 的代谢组学研究，导致分离出三种核糖体合成和翻译后修饰的 II 型硫肽，saalfelduracin B –D ( 1 – 3 ) 和已知的 saalfelduracin A ( 4 )。所有四种化合物的结构均通过比较二维核磁共振分析和高分辨率串联质谱法确定。
• d-Cysteine occurrence in thiostrepton may not necessitate an epimerase
  作者：Sebastian Schoof、Hans-Dieter Arndt

  DOI：10.1039/b912733j

  日期：——

  The natural product thiopeptide antibiotic thiostrepton is shown to undergo facile epimerization at its thiazoline residue in favor of the naturally observed D-configuration, suggesting that a classical epimerase enzyme may not be involved in its biosynthesis.

  研究表明，天然产品硫肽抗生素硫司肽在其噻唑啉残基上发生了简单的表聚作用，而自然观察到的 D-构型则发生了简单的表聚作用，这表明经典的表聚酶可能没有参与其生物合成。