酒色霉素 A1 | 78164-00-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 中文名称: 酒色霉素 A1
• 中文别名: 酒色霉素A1
• 英文名称: vineomycin A₁
• 英文别名: vineomycin A1；P-1894B；(3R,4aR,12bS)-4a,8,12b-trihydroxy-9-[(2R,4R,5S,6R)-4-hydroxy-6-methyl-5-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxyoxan-2-yl]-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
• CAS: 78164-00-8
• 化学式: C₄₉H₅₈O₁₈
• 分子量: 934.989
• InChiKey: YHSTYYHRDFATAQ-XURVNGJNSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  67
• 可旋转键数：
  9
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  249
• 氢给体数：
  4
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  酒色霉素 A1 在 盐酸 作用下， 以 水 为溶剂， 生成 水绫霉素
  参考文献：
  名称：

  Identification of the aglycon part of vineomycin A1 with aquayamycin.

  摘要：

  藤黄霉素 A1（原 OS-4742 A1）由 Streptomyces matensis subsp.通过温和水解得到的苷元部分与水霉素相同，并确定了其 13C-NMR 赋值。

  DOI：

  10.1248/cpb.29.1788
• 作为产物：
  描述：

  在 三羟甲基氨基甲烷盐酸盐 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以8 mg的产率得到
  参考文献：
  名称：

  Identification of the Grincamycin Gene Cluster Unveils Divergent Roles for GcnQ in Different Hosts, Tailoring the l-Rhodinose Moiety

  摘要：

  The gene cluster responsible for grincamycin (GCN, 1) biosynthesis in Streptomyces lusitanus SCSIO LR32 was identified; heterologous expression of the GCN cluster in S. coelicolor M512 yielded P-1894B (1b) as a predominant product. The Delta gcnQ mutant accumulates intermediate la and two shunt products 2a and 3a bearing L-rhodinose for L-cinerulose A substitutions. In vitro data demonstrated that GcnQ is capable of iteratively tailoring the two L-rhodinose moieties into L-aculose moieties, supporting divergent roles of GcnQ in different hosts.

  DOI：

  10.1021/ol401253p

文献信息

• The absolute configuration of P-1894B, a potent prolyl hydroxylase inhibitor.
  作者：KAZUHIKO OHTA、EIJI MIZUTA、HISAYOSHI OKAZAKI、TOYOKAZU KISHI

  DOI：10.1248/cpb.32.4350

  日期：——

  The previous X-ray-crystallographic determination of the relative configuration of P-1894B, a potent prolyl hydroxylase inhibitor isolated from the culture broth of Streptomyces albogriseolus, was extended by means of chemical and spectral studies. The absolute configuration of P-1894B (1) was established from the absolute configuration of two constituent monosaccharides, L-aculose (3) and L-rhodinose (4), produced by chemical degradation of 1. The absolute configuration of the aglycone part (aquayamycin) was also established as 2. The stereostructure of the reduction product (11) obtained by the catalytic hydrogenation of 1 was also elucidated.

  之前对从白色链霉菌的培养液中分离出的强效脯氨酸羟化酶抑制剂P-1894B的相对构型的X射线晶体学测定，通过化学和光谱研究得到了进一步的扩展。通过对1的化学降解所产生的两个组成单糖L-果糖（3）和L-红糖（4）的绝对构型，确定了P-1894B（1）的绝对构型。糖苷部分（aquayamycin）的绝对构型也被确定为2。此外，还阐明了通过对1进行催化加氢反应获得的还原产物（11）的立体结构。
• The absolute configuration of P-1894B (vineomycin A1), a potent prolyl hydroxylase inhibitor.
  作者：Kazuhiko Ohta、Hisayoshi Okazaki、Toyokazu Kishi

  DOI：10.1248/cpb.30.762

  日期：——

  The absolute configuration of P-1894B (vineomycin A1 (I)), a potent prolyl hydroxylase inhibitor, has been established as I from the absolute configuration of two sugar moieties (II, VI) obtained by chemical degradation of I.

  P-1894B （藤黄霉素 A1 (I)）是一种强效的脯氨酰羟化酶抑制剂，通过化学降解 I 得到的两个糖分子（II、VI）的绝对构型，确定其绝对构型为 I。
• Identification of the Grincamycin Gene Cluster Unveils Divergent Roles for GcnQ in Different Hosts, Tailoring the <scp>l</scp>-Rhodinose Moiety
  作者：Yun Zhang、Hongbo Huang、Qi Chen、Minghe Luo、Aijun Sun、Yongxiang Song、Junying Ma、Jianhua Ju

  DOI：10.1021/ol401253p

  日期：2013.7.5

  The gene cluster responsible for grincamycin (GCN, 1) biosynthesis in Streptomyces lusitanus SCSIO LR32 was identified; heterologous expression of the GCN cluster in S. coelicolor M512 yielded P-1894B (1b) as a predominant product. The Delta gcnQ mutant accumulates intermediate la and two shunt products 2a and 3a bearing L-rhodinose for L-cinerulose A substitutions. In vitro data demonstrated that GcnQ is capable of iteratively tailoring the two L-rhodinose moieties into L-aculose moieties, supporting divergent roles of GcnQ in different hosts.
• Identification of the aglycon part of vineomycin A1 with aquayamycin.
  作者：NOBUTAKA IMAMURA、KATSUMI KAKINUMA、NOBUO IKEKAWA、HARUO TANAKA、SATOSHI OMURA

  DOI：10.1248/cpb.29.1788

  日期：——

  Vineomycin A1 (formerly OS-4742 A1) produced by Streptomyces matensis subsp. vineus, is an antibacterial and antitumor antibiotic. The aglycon part obtained by mild hydrolysis turned out to be identical with aquayamycin, and its 13C-NMR assignment was also determined.

  藤黄霉素 A1（原 OS-4742 A1）由 Streptomyces matensis subsp.通过温和水解得到的苷元部分与水霉素相同，并确定了其 13C-NMR 赋值。