O¹-β-D-galactopyranosylchloramphenicol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: O¹-β-D-galactopyranosylchloramphenicol
• 英文别名: chloramphenicol galactoside conjugate；Chloramphenicol 1-O-beta-D-galactopyranoside；2,2-dichloro-N-[(1R,2R)-1-hydroxy-1-(4-nitrophenyl)-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]acetamide
• 化学式: C₁₇H₂₂Cl₂N₂O₁₀
• 分子量: 485.275
• InChiKey: APNJPGQQUGNBMU-PRZACTIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  195
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 48.25h， 生成 O¹-β-D-galactopyranosylchloramphenicol
  参考文献：
  名称：

  SYNTHESIS OF CHLORAMPHENICOL AND MANDELONITRILE GALACTOSE-CONTAINING PRODRUGS

  摘要：

  The synthesis of O-1-beta-D-galactopyranosylchloramphenicol and O-1-beta-D-galactopyranosylmandelonitrile as prodrugs potentially substrates of beta-galactosidase, are reported. Preparation of O-1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl) chloramphenicol from unprotected chloramphenicol was successful using beta-D-galactopyranose pentaacetate and boron trifluoride diethyl etherate in acetonitrile. However, the beta-galactosylated diastereoisomers of racemic mandelonitrile had to be made via O-1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)mandelamide in dichloromethane prior to dehydration to obtain the nitrile moiety. Indeed, galactosylation trials starting directly from mandelonitrile in acetonitrile led to the O-1-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)mandelonitrile diastereoisomers. From a methodological point of view, this work extends the use of the galactosylation method to new hydroxyl bearing compounds. It also points out that the solvent used (acetonitrile or dichloromethane) and the purity of boron trifluoride diethyl etherate can be crucial factors in the use of this method as an eventual alternative to heavy metal-based Lewis acids usually employed in glycosylation reactions.

  DOI：

  10.1081/car-120013493

文献信息

• Compositions and methods for targeted enzymatic release of cell regulatory compounds
  申请人：Marker Gene Technologies, Inc.

  公开号：US06656917B1

  公开（公告）日：2003-12-02

  Novel pro-drugs and methods for their use to alter the growth and biological characteristics of living cells, tissues, or whole organisms are described. The methods allow for selective activation of the pro-drugs at or near transformant host cells expressing a gene for an enzyme that activates the pro-drugs. Pro-drugs according to a preferred embodiment of the invention are conjugates of a bioactive compound and a chemical group that is capable of being cleaved from the bioactive compound by action of an enzyme. Methods according to this invention include, (a) introducing into targeted cells a gene encoding an enzyme and (b) administering a pro-drug, wherein the enzyme releases the pro-drug from conjugation. In a preferred embodiment of the invention, the gene encoding the enzyme is a marker gene.

  本发明描述了新型前药及其用于改变活细胞、组织或整个生物体的生长和生物学特性的方法。该方法允许在表达激活前药酶基因的转化宿主细胞附近或附近选择性地激活前药。根据本发明的一个优选实施例，前药是生物活性化合物与能够通过酶作用从生物活性化合物中裂解出来的化学基团的缀合物。根据本发明的方法包括：(a)将编码酶的基因引入目标细胞；(b)施用前药，其中酶从前药缀合物中释放前药。在本发明的一个优选实施例中，编码酶的基因是标记基因。
• SYNTHESIS OF CHLORAMPHENICOL AND MANDELONITRILE GALACTOSE-CONTAINING PRODRUGS
  作者：Yves L. Janin、Grégory Zoltobroda、Christiane Huel、Claude Monneret

  DOI：10.1081/car-120013493

  日期：2002.9.23

  The synthesis of O-1-beta-D-galactopyranosylchloramphenicol and O-1-beta-D-galactopyranosylmandelonitrile as prodrugs potentially substrates of beta-galactosidase, are reported. Preparation of O-1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl) chloramphenicol from unprotected chloramphenicol was successful using beta-D-galactopyranose pentaacetate and boron trifluoride diethyl etherate in acetonitrile. However, the beta-galactosylated diastereoisomers of racemic mandelonitrile had to be made via O-1-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)mandelamide in dichloromethane prior to dehydration to obtain the nitrile moiety. Indeed, galactosylation trials starting directly from mandelonitrile in acetonitrile led to the O-1-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)mandelonitrile diastereoisomers. From a methodological point of view, this work extends the use of the galactosylation method to new hydroxyl bearing compounds. It also points out that the solvent used (acetonitrile or dichloromethane) and the purity of boron trifluoride diethyl etherate can be crucial factors in the use of this method as an eventual alternative to heavy metal-based Lewis acids usually employed in glycosylation reactions.