methyl 2,3-di-O-acetyl-β-D-ribofuranoside | 116467-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-acetyl-β-D-ribofuranoside
• 英文别名: methyl 2,3-di-O-acetyl-β-D-ribofuranose；[(2R,3R,4R,5R)-4-acetyloxy-2-(hydroxymethyl)-5-methoxyoxolan-3-yl] acetate
• CAS: 116467-00-6
• 化学式: C₁₀H₁₆O₇
• 分子量: 248.233
• InChiKey: WBQLESKADSIWBQ-ZYUZMQFOSA-N

物化性质

• 沸点：
  338.1±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-acetyl-β-D-ribofuranoside 在 吡啶 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 以75%的产率得到α,β-D-ribofuranose-5-phophate disodium salt
  参考文献：
  名称：

  Chemoenzymatic preparation of nucleosides from furanoses

  摘要：

  Chemoenzymatic preparation of ribose, deoxyribose and arabinose 5-phosphates was accomplished. These compounds were tested as starting materials in the enzymatic preparation of natural and modified purine and pyrimidine nucleosides, using an overexpressed Escherichia coli phosphopentomutase. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.087
• 作为产物：
  描述：

  methyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside 在 碘 作用下， 以 甲醇 为溶剂， 以33%的产率得到methyl 2,3-di-O-acetyl-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of aminodisaccharide–nucleoside conjugates for RNA binding

  摘要：

  Two types of aminodisaccharide-nucleoside conjugates were synthesized by the condensation of azidodisaccharide and nucleoside using aliphatic diamine as a linker. The corresponding azidodisaccharides could be yielded from neamine in good yield. The binding properties to 16S RNA of these conjugates were evaluated by SPR. It was found that the nucleobase played a significant role in the binding of these conjugates to 16S RNA and a shorter linker between the aminodisaccharide and nucleoside was favorable for 16S RNA binding. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.002

文献信息

• Synthesis of Well-Defined Adenosine Diphosphate Ribose Oligomers
  作者：Hans A. V. Kistemaker、Lucien N. Lameijer、Nico J. Meeuwenoord、Herman S. Overkleeft、Gijsbert A. van der Marel、Dmitri V. Filippov

  DOI：10.1002/anie.201412283

  日期：2015.4.13

  elucidation of the biology of ADPr, the availability of well‐defined fragments of poly(ADP‐ribose) is essential. Herein we report a solid‐phase synthetic approach for the preparation of ADP‐ribose oligomers of exactly defined length. The methodology is exemplified by the first reported synthesis of an ADP‐ribose dimer and trimer.

  翻译后的蛋白质修饰称为二磷酸腺苷核糖基化（ADPr），可调节多种重要的生物学过程，例如DNA损伤修复和细胞代谢。该修饰也参与致癌作用和衰老过程。因此，更好地了解ADP核糖基化的功能对于开发新型疗法至关重要。为了便于阐明ADPr的生物学特性，必须使用定义明确的聚（ADP-核糖）片段。本文中，我们报告了一种固相合成方法，用于制备长度精确确定的ADP-核糖低聚物。该方法以首次报道的ADP核糖二聚体和三聚体的合成为例。
• Porcine Liver Esterase-Catalyzed Hydrolysis of Methyl Tri-O-acetyl-β-D-arabinopyranoside, Methyl Tri-O-acetyl-β-D-ribopyranoside and Methyl Tri-O-acetyl-β-D-ribofuranoside
  作者：Jitka Moravcová、Karel Kefurt、Romana Hladůvková、Jan Staněk

  DOI：10.1135/cccc20001619

  日期：——

  Methyl 2,3,4-tri-O-acetyl-β-D-arabinopyranoside (1), methyl 2,3,4-tri-O-acetyl-β-D-ribopyranoside (2), and methyl 2,3,5-tri-O-acetyl-β-D-ribofuranoside (3) were deacetylated in porcine liver esterase-catalyzed reactions. Triacetate 1 gave methyl 3,4-di-O-acetyl-β-D-arabinopyranoside in 70% preparative yield while the regioselectivities found for the substrates 2 and 3 were substantially lower. Both the Michaelis constant and maximum rate were calculated for deacetylation of 1, 2, and 3. The results were interpreted using an active site model for the esterase proposed by Jones.

  甲基2,3,4-三<斜体>O-乙酰基-β-D-阿拉比诺吡喃糖苷（<粗体>1）、甲基2,3,4-三<斜体>O-乙酰基-β-D-核糖吡喃糖苷（<粗体>2）和甲基2,3,5-三<斜体>O-乙酰基-β-D-核糖呋喃糖苷（<粗体>3）在猪肝酯酶催化反应中被脱乙酰化。三乙酸酯<粗体>1以70％的制备收率得到甲基3,4-二<斜体>O-乙酰基-β-D-阿拉比诺吡喃糖苷，而对于底物<粗体>2和<粗体>3发现的区域选择性明显较低。计算了<粗体>1、<粗体>2和<粗体>3的脱乙酰化的米氏常数和最大速率。结果使用Jones提出的酯酶活性位点模型进行了解释。
• Enzymes in carbohydrate synthesis. Lipase-catalyzed selective acylation and deacylation of furanose and pyranose derivatives
  作者：William J. Hennen、H. Marcel Sweers、Yi Fong Wang、Chi Huey Wong

  DOI：10.1021/jo00256a008

  日期：1988.10
• Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver
  作者：Gesche Dufner、Ralf Schwörer、Bernd Müller、Richard R. Schmidt

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1467::aid-ejoc1467>3.0.co;2-e

  日期：2000.4

  The reaction of sialyl phosphites 1, 22a-d, 28, 39, and 45 with acyl-protected riboside 5-phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding beta-configured sialyl riboside monophosphates 3a,b, 24a-d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a-d, 30, 48, and 49 is described. Investigations with alpha(2-6)-sialyl-transferase from rat Liver showed that base replacement in CMP-Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5-, 8-, or g-position of the neuraminic acid residue (25a-d, 30, 48, 49) are tolerated.
• Synthesis of aminodisaccharide–nucleoside conjugates for RNA binding
  作者：Li Cai、Qin Li、Bo Ren、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tet.2007.06.002

  日期：2007.8

  Two types of aminodisaccharide-nucleoside conjugates were synthesized by the condensation of azidodisaccharide and nucleoside using aliphatic diamine as a linker. The corresponding azidodisaccharides could be yielded from neamine in good yield. The binding properties to 16S RNA of these conjugates were evaluated by SPR. It was found that the nucleobase played a significant role in the binding of these conjugates to 16S RNA and a shorter linker between the aminodisaccharide and nucleoside was favorable for 16S RNA binding. (c) 2007 Elsevier Ltd. All rights reserved.