(6S,7S,18S)-20-aza-6,10,12,18-tetramethyl-7-O-(2',6'-dideoxy-3'-C-methyl-β-D-ribo-hexopyranosyl)-cycloicosa-2,4,9,12,14-pentaen-1-one | 312532-50-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (6S,7S,18S)-20-aza-6,10,12,18-tetramethyl-7-O-(2',6'-dideoxy-3'-C-methyl-β-D-ribo-hexopyranosyl)-cycloicosa-2,4,9,12,14-pentaen-1-one
• 英文别名: vicenistatin M；(3E,5E,7S,8S,10E,13E,15E,19S)-8-[(2R,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-7,11,13,19-tetramethyl-1-azacycloicosa-3,5,10,13,15-pentaen-2-one
• CAS: 312532-50-6
• 化学式: C₃₀H₄₇NO₅
• 分子量: 501.707
• InChiKey: YVXZXDRTHFRUIX-LPLNQVICSA-N

物化性质

• 沸点：
  672.7±55.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 (6S,7S,18S)-20-aza-6,10,12,18-tetramethyl-7-O-(2',6'-dideoxy-3'-C-methyl-β-D-ribo-hexopyranosyl)-cycloicosa-2,4,9,12,14-pentaen-1-one 在 乙酰氯 作用下， 反应 1.0h， 以74%的产率得到methyl β-mycaroside
  参考文献：
  名称：

  Isolation and Structure Elucidation of Vicenistatin M, and Importance of the Vicenisamine Aminosugar for Exerting Cytotoxicity of Vicenistatin.

  摘要：

  从生产菌株链霉菌属（Streptomyces sp.）HC-34中分离出一种新的维西尼司他汀类似物。已阐明结构的一个特征是存在一种中性糖麦芽糖，而不是维西尼司他汀的氨基糖维西尼司他胺。通过合成D-麦芽糖和维西尼司他汀M本身，确定了新类似物（命名为维西尼司他汀M）的绝对立体化学结构。维西尼司他汀M的生物学测试表明，维西尼司他胺对于发挥维西尼司他汀的细胞毒性至关重要。

  DOI：

  10.7164/antibiotics.54.211
• 作为产物：
  描述：

  (3E,5E,7S,8S,10E,13E,15E,19S)-8-[(2R,4S,5S,6R)-4-羟基-6-甲基-5-甲基氨基四氢吡喃-2-基]氧基-7,11,13,19-四甲基-1-氮杂环二十碳-3,5,10,13,15-五烯-2-酮 在 盐酸 、 氢氧化钾 、 silver perchlorate 、 四氯化锡 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 51.0h， 生成 (6S,7S,18S)-20-aza-6,10,12,18-tetramethyl-7-O-(2',6'-dideoxy-3'-C-methyl-β-D-ribo-hexopyranosyl)-cycloicosa-2,4,9,12,14-pentaen-1-one
  参考文献：
  名称：

  Isolation and Structure Elucidation of Vicenistatin M, and Importance of the Vicenisamine Aminosugar for Exerting Cytotoxicity of Vicenistatin.

  摘要：

  从生产菌株链霉菌属（Streptomyces sp.）HC-34中分离出一种新的维西尼司他汀类似物。已阐明结构的一个特征是存在一种中性糖麦芽糖，而不是维西尼司他汀的氨基糖维西尼司他胺。通过合成D-麦芽糖和维西尼司他汀M本身，确定了新类似物（命名为维西尼司他汀M）的绝对立体化学结构。维西尼司他汀M的生物学测试表明，维西尼司他胺对于发挥维西尼司他汀的细胞毒性至关重要。

  DOI：

  10.7164/antibiotics.54.211

文献信息

• Substrate Flexibility of Vicenisaminyltransferase VinC Involved in the Biosynthesis of Vicenistatin
  作者：Atsushi Minami、Tadashi Eguchi

  DOI：10.1021/ja0685250

  日期：2007.4.1

  A glycosyltransferase VinC is involved in the biosynthesis of antitumor beta-glycoside antibiotic vicenistatin. It catalyzes a glycosyl transfer reaction between dTDP-alpha-D-vicenisamine and vicenilactam. Previous identification of its broad substrate specificity toward various glycosyl acceptors enabled us to explore the potential of VinC for glycodiversification. In vitro study of the substrate specificity toward several dTDP-sugars with vicenilactam established that VinC displayed activities with alpha-anomers of several dTDP-2-deoxy-D-sugars such as mycarose, digitoxose, olivose, and 2-deoxyglucose to afford respective beta-glycosides. Notably, beta-anomers of dTDP-2-deoxy-D-sugars also appeared to be accepted by VinC to form alpha-glycosides. Furthermore, VinC is capable of catalyzing glycosyl transfer reactions from both the alpha-anomer and beta-anomer of dTDP-L-mycarose, respectively, into beta-glycoside and alpha-glycoside. These results indicate that VinC is a unique glycosyltransferase possessing broad substrate specificity. The mechanism of this axially oriented glycosidic bond formation from the equatorially oriented dTDP-sugar might be explained by conformational change of dTDP-sugar to a boat conformation during the glycosyl transfer reaction. To apply these features of VinC for glycodiversification, 22 sets of structurally diverse glycosides were constructed using unnatural glycosyl donors and acceptors.
• Isolation and Structure Elucidation of Vicenistatin M, and Importance of the Vicenisamine Aminosugar for Exerting Cytotoxicity of Vicenistatin.
  作者：YOSHITAKA MATSUSHIMA、TAKUYA NAKAYAMA、MASAKI FUJITA、RENUKA BHANDARI、TADASHI EGUCHI、KAZUTOSHI SHINDO、KATSUMI KAKINUMA

  DOI：10.7164/antibiotics.54.211

  日期：——

  A new analogue of Vicenistatin was isolated from the producing strain Streptomyces sp. HC-34. A characteristic of the elucidated structure involved the existence of a neutral sugar mycarose instead of an aminosugar vicenisamine of Vicenistatin. The absolute stereochemistry of the new analogue (named as Vicenistatin M) was determined by the synthesis of D-mycarose and of vicenistatin M itself. Biological testing of Vicenistatin M suggested the importance of vicenisamine for exerting the cytotoxicity of vicenistatin.

  从生产菌株链霉菌属（Streptomyces sp.）HC-34中分离出一种新的维西尼司他汀类似物。已阐明结构的一个特征是存在一种中性糖麦芽糖，而不是维西尼司他汀的氨基糖维西尼司他胺。通过合成D-麦芽糖和维西尼司他汀M本身，确定了新类似物（命名为维西尼司他汀M）的绝对立体化学结构。维西尼司他汀M的生物学测试表明，维西尼司他胺对于发挥维西尼司他汀的细胞毒性至关重要。