(S)-2-Azido-3-acetamidopropanal | 150571-20-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-Azido-3-acetamidopropanal
• 英文别名: N-[(2S)-2-azido-3-oxopropyl]acetamide
• CAS: 150571-20-3
• 化学式: C₅H₈N₄O₂
• 分子量: 156.144
• InChiKey: MMMYHNNYSAXDMR-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Azido-3-acetamidopropanal 在 palladium on activated charcoal 盐酸 、 氢气 、 三羟甲基氨基甲烷 、 sodium chloride 作用下， 以 乙醇 、 水 为溶剂， 37.0 ℃ 、392.24 kPa 条件下， 反应 26.0h， 生成 1-acetamido-1,2,5-trideoxy-2,5-imino-D-glucitol
  参考文献：
  名称：

  Inhibition of N-acetylglucosaminyl transfer enzymes: chemical-enzymic synthesis of new five-membered acetamido azasugars

  摘要：

  Two new acetamido azasugars have been synthesized and tested as inhibitors of beta-N-acetylglucosaminase. Ozonolysis of enantiomerically pure N-(4-phenyl-2-azido-3-butenyl)acetamide, derived from cinnamic aldehyde, followed by lipase-catalyzed resolution of the amine intermediate 5, gave 2-azido-3-acetamidopropanal which was then condensed with dihydroxyacetone phosphate by using FDP-aldolase. The condensed product was dephosphorylated and hydrogenated to afford the five-membered acetamido azasugar analogous to N-acetylglucosamine. Compounds 1 and 2 prepared in this manner were new competitive inhibitors of a beta-N-acetylglucosaminidase with K(i) values of 1.9 and 3.6 muM, respectively, and could be useful for the synthesis of N-acetylglucosaminyltransferase inhibitors.

  DOI：

  10.1021/jo00070a013
• 作为产物：
  描述：

  (R)-N-(4-Phenyl-2-azido-3-butenyl)acetamide 在 二甲基硫 、 臭氧 作用下， 以 甲醇 为溶剂， 生成 (S)-2-Azido-3-acetamidopropanal
  参考文献：
  名称：

  Inhibition of N-acetylglucosaminyl transfer enzymes: chemical-enzymic synthesis of new five-membered acetamido azasugars

  摘要：

  Two new acetamido azasugars have been synthesized and tested as inhibitors of beta-N-acetylglucosaminase. Ozonolysis of enantiomerically pure N-(4-phenyl-2-azido-3-butenyl)acetamide, derived from cinnamic aldehyde, followed by lipase-catalyzed resolution of the amine intermediate 5, gave 2-azido-3-acetamidopropanal which was then condensed with dihydroxyacetone phosphate by using FDP-aldolase. The condensed product was dephosphorylated and hydrogenated to afford the five-membered acetamido azasugar analogous to N-acetylglucosamine. Compounds 1 and 2 prepared in this manner were new competitive inhibitors of a beta-N-acetylglucosaminidase with K(i) values of 1.9 and 3.6 muM, respectively, and could be useful for the synthesis of N-acetylglucosaminyltransferase inhibitors.

  DOI：

  10.1021/jo00070a013

文献信息

• Inhibition of N-acetylglucosaminyl transfer enzymes: chemical-enzymic synthesis of new five-membered acetamido azasugars
  作者：Yoshikazu Takaoka、Tetsuya Kajimoto、Chi Huey Wong

  DOI：10.1021/jo00070a013

  日期：1993.8

  Two new acetamido azasugars have been synthesized and tested as inhibitors of beta-N-acetylglucosaminase. Ozonolysis of enantiomerically pure N-(4-phenyl-2-azido-3-butenyl)acetamide, derived from cinnamic aldehyde, followed by lipase-catalyzed resolution of the amine intermediate 5, gave 2-azido-3-acetamidopropanal which was then condensed with dihydroxyacetone phosphate by using FDP-aldolase. The condensed product was dephosphorylated and hydrogenated to afford the five-membered acetamido azasugar analogous to N-acetylglucosamine. Compounds 1 and 2 prepared in this manner were new competitive inhibitors of a beta-N-acetylglucosaminidase with K(i) values of 1.9 and 3.6 muM, respectively, and could be useful for the synthesis of N-acetylglucosaminyltransferase inhibitors.