Ganefromycin α

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ganefromycin α
• 英文别名: (2E,4E,6E)-7-[5-[(4E,6E)-8-[[2-[(2R,3R,4R,6S)-2,4-dihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]-3-(2-phenylacetyl)oxyoxan-2-yl]-3-[(2R,4S,5R,6S)-5-[(2R,4R,5S,6S)-5-[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxypropanoyl]amino]-3-methoxy-4-methylocta-4,6-dien-2-yl]-3-hydroxyoxolan-2-yl]hepta-2,4,6-trienoic acid
• 化学式: C₆₅H₉₅NO₂₁
• 分子量: 1226.46
• InChiKey: UDVVGDCMWCVRCO-DDGPWOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  87
• 可旋转键数：
  29
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  284
• 氢给体数：
  6
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  Ganefromycin α 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以17%的产率得到
  参考文献：
  名称：

  Chemistry and structure of ganefromycin

  摘要：

  Ganefromycins are antibiotics produced by Streptomyces lydicus sp. tanzanius having commercial potential as performance enhancement agents for livestock. Ganefromycins are related to the elfamycin family of antibiotics but contain several unique chemical features which are the source of novel and unexpected chemistry. Reactions under mildly basic conditions resulted in the interconversion of ganefromycins alpha (1) and beta (2) by a 1,2-acyl migration. Strong base causes elimination of a trisaccharide whose structure was solved by single-crystal X-ray diffraction analysis of the triacetate of the reduced ring-opened triol. Ammonolysis yields the same rearranged product from either 1 or 2. Evidence is provided for the mechanism of this rearrangement involving elimination of the saccharide to form a transient alpha,beta-unsaturated carbonyl, Michael addition of ammonia, and intramolecular transacylation. Ozonolysis and acidic methanolysis were employed to obtain simplified compounds for structure determination. Ganefromycin beta fragments in warm acetic acid solution, releasing the long-chain amino acid. C-13 NMR data with assignments are provided for the degradation products.

  DOI：

  10.1021/jo00076a016

文献信息

• Chemistry and structure of ganefromycin
  作者：Guy T. Carter、Douglas W. Phillipson、Robert R. West、Donald B. Borders

  DOI：10.1021/jo00076a016

  日期：1993.11

  Ganefromycins are antibiotics produced by Streptomyces lydicus sp. tanzanius having commercial potential as performance enhancement agents for livestock. Ganefromycins are related to the elfamycin family of antibiotics but contain several unique chemical features which are the source of novel and unexpected chemistry. Reactions under mildly basic conditions resulted in the interconversion of ganefromycins alpha (1) and beta (2) by a 1,2-acyl migration. Strong base causes elimination of a trisaccharide whose structure was solved by single-crystal X-ray diffraction analysis of the triacetate of the reduced ring-opened triol. Ammonolysis yields the same rearranged product from either 1 or 2. Evidence is provided for the mechanism of this rearrangement involving elimination of the saccharide to form a transient alpha,beta-unsaturated carbonyl, Michael addition of ammonia, and intramolecular transacylation. Ozonolysis and acidic methanolysis were employed to obtain simplified compounds for structure determination. Ganefromycin beta fragments in warm acetic acid solution, releasing the long-chain amino acid. C-13 NMR data with assignments are provided for the degradation products.