Acetic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-formyl-6-[2-(3-methyl-3H-diazirin-3-yl)-ethylsulfanyl]-tetrahydro-pyran-4-yl ester | 144152-07-8

• 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: Acetic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-formyl-6-[2-(3-methyl-3H-diazirin-3-yl)-ethylsulfanyl]-tetrahydro-pyran-4-yl ester
• CAS: 144152-07-8
• 化学式: C₁₆H₂₂N₂O₈S
• 分子量: 402.425
• InChiKey: QLQGNXPDAYZJFJ-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  129.92
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-formyl-6-[2-(3-methyl-3H-diazirin-3-yl)-ethylsulfanyl]-tetrahydro-pyran-4-yl ester 在 吡啶 、 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium methylate 作用下， 生成 (2R,3R,4S,5S,6R)-2-[2-(3-Methyl-3H-diazirin-3-yl)-ethylsulfanyl]-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Studies of the interaction of the maltose-binding protein of Escherichia coli, a closed-groove binder, with 4,6-O-ethylidenemalto-oligosaccharides (dp 2–5) and its regioselective labelling with 3-azibutyl 1-thio-α-(6-3H)maltoside

  摘要：

  Four malto-oligosaccharides (dp 2-5), each with a 4,6-O-ethylidene group on the glucosyl unit at the non-reducing terminus, were synthesised and used to prove that the maltose-binding protein (MBP) of E. coli is a closed-groove binder. Alpha-D-glucosylation of 3-azibutyl 1-thio-alpha-D-(6-H-3)glucopyranoside yielded a H-3-labelled, photolabile 1-thiomaltoside derivative that was used to chemically modify the binding site of MBP. The H-3-labelled peptide containing 83% of the total radioactivity, which was isolated after tryptic cleavage of the modified MBP and sequenced, is part of the closed end of the MBP groove.

  DOI：

  10.1016/s0008-6215(00)90995-9
• 作为产物：
  描述：

  3-azibutyl 2,3,4-tri-O-acetyl-1-thio-6-O-triphenylmethyl-α-D-glucopyranoside 在 三甲基氯硅烷 、 磷酸 、 水 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 sodium iodide 作用下， 反应 0.08h， 生成 Acetic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-formyl-6-[2-(3-methyl-3H-diazirin-3-yl)-ethylsulfanyl]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Studies of the interaction of the maltose-binding protein of Escherichia coli, a closed-groove binder, with 4,6-O-ethylidenemalto-oligosaccharides (dp 2–5) and its regioselective labelling with 3-azibutyl 1-thio-α-(6-3H)maltoside

  摘要：

  Four malto-oligosaccharides (dp 2-5), each with a 4,6-O-ethylidene group on the glucosyl unit at the non-reducing terminus, were synthesised and used to prove that the maltose-binding protein (MBP) of E. coli is a closed-groove binder. Alpha-D-glucosylation of 3-azibutyl 1-thio-alpha-D-(6-H-3)glucopyranoside yielded a H-3-labelled, photolabile 1-thiomaltoside derivative that was used to chemically modify the binding site of MBP. The H-3-labelled peptide containing 83% of the total radioactivity, which was isolated after tryptic cleavage of the modified MBP and sequenced, is part of the closed end of the MBP groove.

  DOI：

  10.1016/s0008-6215(00)90995-9