(β-D-galactopyranosyl)-(1-5')-O-2'-deoxy-β-D-ribofuranosyluracil

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (β-D-galactopyranosyl)-(1-5')-O-2'-deoxy-β-D-ribofuranosyluracil
• 英文别名: Gal(b1-5)2-deoxy-D-eryPenf(b)-uracil-1-yl；1-[(2R,4S,5R)-4-hydroxy-5-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₁₅H₂₂N₂O₁₀
• 分子量: 390.347
• InChiKey: HAIUFVQFXBHGBY-YHOIAXGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  178
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (β-D-galactopyranosyl)-(1-5')-O-2'-deoxy-β-D-ribofuranosyluracil 在 吡啶 作用下， 反应 10.0h， 生成 (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-5')-O-3'-O-acetyl-2'-deoxy-β-D-ribofuranosyluracil
  参考文献：
  名称：

  使用β-半乳糖苷酶进行半乳糖基化：二糖核苷的酶促合成

  摘要：

  通过利用米曲霉中β-半乳糖苷酶的反式半乳糖基化潜力，已经实现了各种含半乳糖的二糖核苷的合成。因此，使用对硝基苯基-β-D-半乳糖苷1作为半乳糖基供体，已证明2-脱氧尿苷2a，尿苷2b，胸苷2c和腺苷2d对于酶催化的二糖核苷形成是有用的受体。乙酰化后形成的产物4a-4d的区域化学已经使用现代NMR技术明确分配。

  DOI：

  10.1016/0957-4166(95)00216-c
• 作为产物：
  描述：

  2-脱氧尿苷 、 尾-D-Galactoside,2-nitrophenyl(9CI) 在 β-galactosidase 作用下， 反应 30.0h， 以68%的产率得到(β-D-galactopyranosyl)-(1-5')-O-2'-deoxy-β-D-ribofuranosyluracil
  参考文献：
  名称：

  Facile and regioselective enzymatic 5′-galactosylation of pyrimidine 2′-deoxynucleosides catalyzed by β-glycosidase from bovine liver

  摘要：

  A regioselective enzymatic approach to 5'-O-galactosylated derivatives of pyrimidine 2'-deoxynucleosides was described. With o-nitrophenyl beta-D-galactoside as glycosyl donor, galactosylation reactions of 2'-deoxynucleosides were mediated by a commercial beta-galactosidase from bovine liver, affording 5'-O-galactosylated derivatives with the yields of 45-85% and 5'-regioselectivities of 92-100%. The study of enzyme substrate recognition revealed that the beta-galactosidase performance showed a clear dependence on R-group present in the base moiety of 2'-deoxynucleoside. Besides, such desirable products were synthesized with satisfactory yields (41-68%) and moderate to high 5'-regioselectivities (87-100%) by using the crude enzyme extract. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.03.018

文献信息

• Precisely regulated galactosylation of nucleoside analogues in aqueous hydrophilic solvents catalyzed by solvent-stable β-galactosidase
  作者：Youzhi Zhou、Jianlin Chu、Jinsong Zhang、Ke Liu、Bingfang He

  DOI：10.1039/c6ra12167e

  日期：——

  digalactosyl nucleoside analogues in the buffer system. The addition of DMSO not only prominently increased the stabilization of β-galactosidase but also regulated the products from complicated products to unitary monogalactosyl nucleoside analogues, which could significantly simplify the process of subsequent separation. Strikingly, the affinity of β-galactosidase to 3′-azido-3′-deoxythymidine in 10% DMSO was

  在10％DMSO溶剂系统中成功地合成了有效的合成β-半乳糖基核苷类似物，该方法由耐溶剂的巨大芽孢杆菌中新分离的溶剂稳定的β-半乳糖苷酶催化YZ08。用于核苷类似物的半乳糖基化的最有效的糖供体是乳糖而不是硝基苯基糖苷。然而，它伴随着在缓冲系统中形成复杂的二半乳糖基核苷类似物。DMSO的加入不仅显着提高了β-半乳糖苷酶的稳定性，而且还调节了从复杂产物到单一单半乳糖基核苷类似物的产物，这可以显着简化后续分离的过程。令人惊讶的是，在10％DMSO中，β-半乳糖苷酶对3'-叠氮基3'-脱氧胸苷的亲和力显着增强，催化效率（k cat / K m与缓冲溶液相比）增加了一倍。这些结果表明，通过调节反应溶剂系统，溶剂稳定的糖苷酶在生物合成以及糖苷前药的调节中具有诱人的效力。
• Facile and regioselective enzymatic 5′-galactosylation of pyrimidine 2′-deoxynucleosides catalyzed by β-glycosidase from bovine liver
  作者：Min Ye、Li-Qiang Yan、Ning Li、Min-Hua Zong

  DOI：10.1016/j.molcatb.2012.03.018

  日期：2012.7

  A regioselective enzymatic approach to 5'-O-galactosylated derivatives of pyrimidine 2'-deoxynucleosides was described. With o-nitrophenyl beta-D-galactoside as glycosyl donor, galactosylation reactions of 2'-deoxynucleosides were mediated by a commercial beta-galactosidase from bovine liver, affording 5'-O-galactosylated derivatives with the yields of 45-85% and 5'-regioselectivities of 92-100%. The study of enzyme substrate recognition revealed that the beta-galactosidase performance showed a clear dependence on R-group present in the base moiety of 2'-deoxynucleoside. Besides, such desirable products were synthesized with satisfactory yields (41-68%) and moderate to high 5'-regioselectivities (87-100%) by using the crude enzyme extract. (C) 2012 Elsevier B.V. All rights reserved.
• Galactosylation by use of β-galactosidase: Enzymatic syntheses of disaccharide nucleosides
  作者：Wolfgang H. Binder、Hanspeter Kählig、Walther Schmid

  DOI：10.1016/0957-4166(95)00216-c

  日期：1995.7

  synthesis of various galactose containing disaccharide nucleosides has been achieved by utilizing the transgalactosylation potential of ß-galactosidase from Aspergillus oryzae. Thus, using p-nitrophenyl-ß-D-galactoside 1 as galactosyl donor, 2-deoxyuridine 2a, uridine 2b, thymidine 2c and adenosine 2d have proven to be useful acceptors for the enzyme catalyzed disaccharide nucleoside formation. The regiochemistry

  通过利用米曲霉中β-半乳糖苷酶的反式半乳糖基化潜力，已经实现了各种含半乳糖的二糖核苷的合成。因此，使用对硝基苯基-β-D-半乳糖苷1作为半乳糖基供体，已证明2-脱氧尿苷2a，尿苷2b，胸苷2c和腺苷2d对于酶催化的二糖核苷形成是有用的受体。乙酰化后形成的产物4a-4d的区域化学已经使用现代NMR技术明确分配。