allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-O-(imidazolylthiocarbonyl)-α-D-galactopyranosiduronamide | 220974-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-O-(imidazolylthiocarbonyl)-α-D-galactopyranosiduronamide
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[(2S,3R,4S,5R,6S)-6-carbamoyl-4-carbamoyloxy-5-(imidazole-1-carbothioyloxy)-2-prop-2-enoxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 220974-56-1
• 化学式: C₂₈H₃₇N₅O₁₅S
• 分子量: 715.692
• InChiKey: AGQWZBOKAHAUCL-RXMNFJGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.68
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  267.38
• 氢给体数：
  3.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-O-(imidazolylthiocarbonyl)-α-D-galactopyranosiduronamide 在 偶氮二异丁腈 、 三正丁基氢锡 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.0h， 生成 3-oxopropyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-deoxy-α-D-xylo-hexopyranosiduronamide
  参考文献：
  名称：

  Synthesis and transglycosylase-inhibiting properties of a disaccharide analogue of moenomycin A lacking substitution at C-4 of unit F

  摘要：

  A disaccharide analogue (A4 = 13c) of moenomycin A lacking the OH group in the 4-position of the uronic acid moiety has been synthesized using the Saito deoxygenation reaction as key step. 13c does not inhibit the transglycosylase (PBP 1b), a key enzyme in the biosynthesis of bacterial peptidoglycan. The result demonstrates the importance of this OH group for the binding of disaccharide moenomycin analogues to the enzyme. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01225-3
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3R,4S,5R,6S)-2-allyloxy-6-carbamoyl-5-hydroxy-4-trichloromethylcarbamoyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester 在 N,N-二甲基甲酰胺 、 锌 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-O-(imidazolylthiocarbonyl)-α-D-galactopyranosiduronamide
  参考文献：
  名称：

  Synthesis and transglycosylase-inhibiting properties of a disaccharide analogue of moenomycin A lacking substitution at C-4 of unit F

  摘要：

  A disaccharide analogue (A4 = 13c) of moenomycin A lacking the OH group in the 4-position of the uronic acid moiety has been synthesized using the Saito deoxygenation reaction as key step. 13c does not inhibit the transglycosylase (PBP 1b), a key enzyme in the biosynthesis of bacterial peptidoglycan. The result demonstrates the importance of this OH group for the binding of disaccharide moenomycin analogues to the enzyme. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01225-3