O-(2-deoxy-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-glucopyranose | 145146-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2-deoxy-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-glucopyranose
• 英文别名: 2-Deoxy-D-galactopyranosyl-β(1,4)-2-acetamido-2-deoxy-D-glucopyranose；2-deoxy-D-galactopyranosyl-β(1,4)-2-acetamido-2-deoxyglucopyranose；2-deoxy-D-lyxo-hexopyranosyl-(1->4)-2-acetamido-2-deoxy-D-glucopyranose；2'-deoxy-N-acetyllactosamine；N-[(3R,4R,5S,6R)-5-[(2S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 145146-83-4
• 化学式: C₁₄H₂₅NO₁₀
• 分子量: 367.353
• InChiKey: AUHJBABGJRWWEH-USQDQHIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  178
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 O-(2-deoxy-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-glucopyranose 在 吡啶 作用下， 生成 3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hexopyranosyl-(1->4)-1,3,6-tri-O-acetyl-2-acetamido-2-deoxy-α/β-D-glucopyranose
  参考文献：
  名称：

  En route to deoxygenated N-acetyllactosamine analogues employing uridyl and galactosyl transferases

  摘要：

  All monodeoxygenated galactoses were treated with galactokinase, and for the 2-, 3-, and 4-deoxy compounds, transformation into the corresponding galactopyranosyl phosphates could be observed. In case of the 2-deoxy derivative, further reaction via UDP-2-deoxy-D-lyxo-hexose (UDP-2-deoxygalactose), which was also obtained chemically, the multiple enzymatic system could be employed to prepare 2'-deoxy-N-acetyllactosamine. (C) 2009 Elsevier Ltd. Ail rights reserved.

  DOI：

  10.1016/j.carres.2009.05.015
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 尿苷-5'-三磷酸 作用下， 以 水 为溶剂， 反应 144.0h， 生成 O-(2-deoxy-β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Galactose-Terminated Oligosaccharides by Use of Galactosyltransferase

  摘要：

  半乳糖基转移酶分别催化以葡萄糖和2-乙酰胺基-2-脱氧吡喃葡萄糖为末端的多糖的半乳糖基化反应。本文描述了关于受体底物和供体底物的变化。

  DOI：

  10.1055/s-1992-34174

文献信息

• Process for the enzymatic synthesis of 2-deoxy-.beta.-D-galactosides
  申请人：Hoechst Aktiengesellschaft

  公开号：US05264352A1

  公开（公告）日：1993-11-23

  The invention relates to a process for the enzymatic synthesis of 2-deoxy-.beta.-D-galactosides. The enzyme galactosyltransferase is able to catalyze the transfer of 2-deoxygalactose residues from the donor substrate uridine 5'-diphospho-2-deoxy-D-galactose to N-acetylglucosamine or aspartyl-N-acetylglucosamine or, in the presence of lactose, to terminal glucose.

  本发明涉及一种酶促合成2-脱氧-β-D-半乳糖苷的方法。半乳糖转移酶能够催化将供体底物尿苷5'-二磷酸-2-脱氧-D-半乳糖酰基转移至N-乙酰氨基葡萄糖或天冬氨酰-N-乙酰氨基葡萄糖，或在乳糖存在的情况下转移至末端葡萄糖。
• Verfahren zur enzymatischen Synthese von 2-Desoxy-beta-D-galactosiden
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0508346A2

  公开（公告）日：1992-10-14

  Die Erfindung betrifft ein Verfahren zur enzymatischen Synthese von 2-Desoxy-β-D-galactosiden. Das Enzym Galactosyltransferase ist in der Lage, die Übertragung der 2-Desoxygalactosereste von dem Donorsubstrat Uridin-5'-diphospho-2-desoxy-D-galactose auf N-Acetylglucosamin bzw. Aspartyl-N-acetylglucosamin oder, in Anwesenheit von Lactose, auf terminale Glucose zu katalysieren.

  本发明涉及一种酶法合成 2-脱氧-β-D-半乳糖苷的工艺。半乳糖基转移酶能催化供体底物尿苷-5'-二磷酸-2-脱氧-D-半乳糖的 2-脱氧半乳糖残基向 N-乙酰葡糖胺或天冬氨酰-N-乙酰葡糖胺转移，或在有乳糖的情况下，向末端葡萄糖转移。
• Ichikawa, Yoshitaka; Lin, Ying-Chih; Dumas, David P., Journal of the American Chemical Society, 1992, vol. 114, # 24, p. 9283 - 9298
  作者：Ichikawa, Yoshitaka、Lin, Ying-Chih、Dumas, David P.、Shen, Gwo-Jenn、Garcia-Junceda, Eduardo、Williams, Mark A.、Bayer, Robert、Ketcham, Catherine、Walker, Leslie E.、Paulson, James C.、Wong, Chi-Huey

  DOI：——

  日期：——
• Regeneration of sugar nucleotide for enzymic oligosaccharide synthesis: use of Gal-1-phosphate uridyltransferase in the regeneration of UDP-galactose, UDP-2-deoxygalactose, and UDP-galactosamine
  作者：Chi Huey Wong、Ruo Wang、Yoshitaka Ichikawa

  DOI：10.1021/jo00042a008

  日期：1992.7

  A new multiple enzymatic system containing galactose-1-phosphate uridyltransferase suitable for the regeneration of UDP-Gal, UDP-2-deoxy-Gal, and UDP-galactosamine for the synthesis of N-acetyllactosamine and analogs has been developed.
• US5264352A
  申请人：——

  公开号：US5264352A

  公开（公告）日：1993-11-23