orotic acid N-hydroxysuccinimide ester | 74019-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: orotic acid N-hydroxysuccinimide ester
• 英文别名: N-(orotidyloxy)succinimide；(2,5-dioxopyrrolidin-1-yl) 2,4-dioxo-1H-pyrimidine-6-carboxylate
• CAS: 74019-78-6
• 化学式: C₉H₇N₃O₆
• 分子量: 253.171
• InChiKey: VSLIXKCLVCVGMU-UHFFFAOYSA-N

物化性质

• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  orotic acid N-hydroxysuccinimide ester 在 N-甲基吗啉 、 盐酸 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 Ort-Leu-Leu-OH
  参考文献：
  名称：

  Anticandidal activity of pyrimidine-peptide conjugates

  摘要：

  The ability of conjugates of peptides and 5-fluorocytosine or 5-fluoroorotic acid to enter Candida albicans was investigated. A number of conjugates of 5-fluoroorotic acid and peptides were synthesized using 1-(ethoxy-carbonyl)-2-ethoxy-1,2-dihydroquinoline as the coupling agent. Orotyl-L-leucyl-L-leucine, 5-fluoro-4-(N-succinamoyl-L-alanyl-L-leucine)-2(1H)-pyrimidinone [a 5-fluorocytosine derivative], and 5-fluoroorotyl-L-leucyl-L-leucine all inhibited the uptake of trimethionine into C. albicans WD 18-4. Inhibition by 5-fluoroorotyl-L-leucyl-L-leucine was competitive as judged using double-reciprocal plots. Evaluation of minimum inhibitory concentrations of peptide-5-fluorocytosine conjugates suggest that these conjugates enter C. albicans in the intact form. These results provide the first experimental evidence that peptides can carry pyrimidines into a eukaryote.

  DOI：

  10.1021/jm00182a019
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 乳清酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 以54%的产率得到orotic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  Anticandidal activity of pyrimidine-peptide conjugates

  摘要：

  The ability of conjugates of peptides and 5-fluorocytosine or 5-fluoroorotic acid to enter Candida albicans was investigated. A number of conjugates of 5-fluoroorotic acid and peptides were synthesized using 1-(ethoxy-carbonyl)-2-ethoxy-1,2-dihydroquinoline as the coupling agent. Orotyl-L-leucyl-L-leucine, 5-fluoro-4-(N-succinamoyl-L-alanyl-L-leucine)-2(1H)-pyrimidinone [a 5-fluorocytosine derivative], and 5-fluoroorotyl-L-leucyl-L-leucine all inhibited the uptake of trimethionine into C. albicans WD 18-4. Inhibition by 5-fluoroorotyl-L-leucyl-L-leucine was competitive as judged using double-reciprocal plots. Evaluation of minimum inhibitory concentrations of peptide-5-fluorocytosine conjugates suggest that these conjugates enter C. albicans in the intact form. These results provide the first experimental evidence that peptides can carry pyrimidines into a eukaryote.

  DOI：

  10.1021/jm00182a019

文献信息

• Multifunctional dinucleotide analogs for the generation of complex RNA conjugates
  作者：Felix Hausch、Andres Jäschke

  DOI：10.1016/s0040-4020(00)01114-5

  日期：2001.2

  Oligonucleotide conjugates are needed for in vitro selection schemes aiming at reactions between small, organic reactants. A general strategy is provided for the generation of the required RNA reactant conjugates based on multifunctional dinucleotide analogs. These modified dinucleotides allow for enzymatic ligation to native or enzymatically transcribed RNAs. They further contain a flexible polyethylene glycol spacer for correct spatial positioning and a photolabile cleavage site for selective release. The dinucleotides can be derivatized with the desired organic compounds by activated ester chemistry as was demonstrated by coupling to several nucleobases and nucleotides. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Anticandidal activity of pyrimidine-peptide conjugates
  作者：Jen-Shing Ti、Alvin S. Steinfeld、Fred Naider、Ali Gulumoglu、Sam V. Lewis、Jeffrey M. Becker

  DOI：10.1021/jm00182a019

  日期：1980.8

  The ability of conjugates of peptides and 5-fluorocytosine or 5-fluoroorotic acid to enter Candida albicans was investigated. A number of conjugates of 5-fluoroorotic acid and peptides were synthesized using 1-(ethoxy-carbonyl)-2-ethoxy-1,2-dihydroquinoline as the coupling agent. Orotyl-L-leucyl-L-leucine, 5-fluoro-4-(N-succinamoyl-L-alanyl-L-leucine)-2(1H)-pyrimidinone [a 5-fluorocytosine derivative], and 5-fluoroorotyl-L-leucyl-L-leucine all inhibited the uptake of trimethionine into C. albicans WD 18-4. Inhibition by 5-fluoroorotyl-L-leucyl-L-leucine was competitive as judged using double-reciprocal plots. Evaluation of minimum inhibitory concentrations of peptide-5-fluorocytosine conjugates suggest that these conjugates enter C. albicans in the intact form. These results provide the first experimental evidence that peptides can carry pyrimidines into a eukaryote.