12-[N-(5-oxohexanoyl)-glycinyl-l-glutamyl-glycinyl-glycinyl]-aminododecyl 2-acetamido-2-deoxy-β-d-glucopyranoside | 1599472-12-4

• 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: 12-[N-(5-oxohexanoyl)-glycinyl-l-glutamyl-glycinyl-glycinyl]-aminododecyl 2-acetamido-2-deoxy-β-d-glucopyranoside
• CAS: 1599472-12-4
• 化学式: C₃₇H₆₄N₆O₁₄
• 分子量: 816.947
• InChiKey: DIKXQKNADADWPE-BCEWRLIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.58
• 重原子数：
  57.0
• 可旋转键数：
  31.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  308.12
• 氢给体数：
  10.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  尿苷 5’-二二氧磷基半乳糖二钠盐 、 12-[N-(5-oxohexanoyl)-glycinyl-l-glutamyl-glycinyl-glycinyl]-aminododecyl 2-acetamido-2-deoxy-β-d-glucopyranoside 在 β1,4-galactosyltransferase 、 γ-环糊精 、 manganese(ll) chloride 作用下， 以 aq. buffer 为溶剂， 反应 5.0h， 以87%的产率得到12-[N-(5-oxohexanoyl)-glycinyl-l-glutamyl-glycinyl-glycinyl]-aminododecyl O-(β-d-galactopyranosyl)-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside
  参考文献：
  名称：

  Studies of cyclodextrin effect for glycosylation by galactosyltransferase

  摘要：

  Cyclodextrins (CDs) do not disturb HPLC purification and do not form lather, which makes them superior to commonly used surfactants. In this paper, the authors describe the utility of CDs, specifically alpha-CD, beta-CD, and gamma-CD, for the synthesis of neoglycolipids from insoluble peptide-linked substrates. gamma-CD was found to be well matched to the bulky benzyl group and accelerated the reaction for the substrate having Phe (F), while beta-CD was well matched to the methyl group and accelerated the reaction for the substrate having Ala (A). Galactosylation to water-insoluble peptide-linked glucosaminide substrate by galactosyltransferase proceeded 63% at the most, but using either beta-CD or gamma-CD gave quantitative yield within 10 h. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.058
• 作为产物：
  描述：

  芴甲氧羰基-L-谷氨酸-Γ-苄脂 在 palladium 10% on activated carbon 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.55h， 生成 12-[N-(5-oxohexanoyl)-glycinyl-l-glutamyl-glycinyl-glycinyl]-aminododecyl 2-acetamido-2-deoxy-β-d-glucopyranoside
  参考文献：
  名称：

  Studies of cyclodextrin effect for glycosylation by galactosyltransferase

  摘要：

  Cyclodextrins (CDs) do not disturb HPLC purification and do not form lather, which makes them superior to commonly used surfactants. In this paper, the authors describe the utility of CDs, specifically alpha-CD, beta-CD, and gamma-CD, for the synthesis of neoglycolipids from insoluble peptide-linked substrates. gamma-CD was found to be well matched to the bulky benzyl group and accelerated the reaction for the substrate having Phe (F), while beta-CD was well matched to the methyl group and accelerated the reaction for the substrate having Ala (A). Galactosylation to water-insoluble peptide-linked glucosaminide substrate by galactosyltransferase proceeded 63% at the most, but using either beta-CD or gamma-CD gave quantitative yield within 10 h. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.058