methyl-(4,5,7,8,9-penta-O-acetyl-3-deoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate | 142644-35-7

• 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: methyl-(4,5,7,8,9-penta-O-acetyl-3-deoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosonate；methyl (2S,4S,5R,6R)-4,5-diacetyloxy-2-hydroxy-6-[(1R,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 142644-35-7
• 化学式: C₂₀H₂₈O₁₄
• 分子量: 492.434
• InChiKey: XWTAQBXQXILAEH-DCDDNHAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  187
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl-(4,5,7,8,9-penta-O-acetyl-3-deoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.17h， 生成 triethylammonium (N-acetyl-2',3'-di-O-acetylcytidin-5'-yl) [methyl (4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosyl)onate] phosphate
  参考文献：
  名称：

  Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

  摘要：

  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.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1467::aid-ejoc1467>3.0.co;2-e
• 作为产物：
  描述：

  Methyl (phenyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以96%的产率得到methyl-(4,5,7,8,9-penta-O-acetyl-3-deoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  细菌α-（2→6）-唾液酸转移酶的酶促合成Kdn寡糖

  摘要：

  摘要研究了CMP-脱氨基神经氨酸（CMP-β-d-Kdn）的合成及其利用细菌α-（2→6）-唾液酸转移酶的酶促转移反应。CMP-β-d-Kdn由24％的4,5,7,8,9-戊基-乙酰基-3-脱氧-d-甘油-β-d-半乳糖-2-壬基吡喃磺酸酯（2）制备总产量。用CMP-β-d-Kdn（10.2μmol），甲基β-d-内酰胺酶（7，8.1μmol）和纯化的唾液酸转移酶（80 munits）酶促合成Kdn低聚糖，得到Kdn-α-（2→6）-Gal β-（1→4）-GlcNAc-β-1-OMe的产率为77％。

  DOI：

  10.1016/s0008-6215(98)00331-0

文献信息

• Microbial Glycosyltransferases for Carbohydrate Synthesis:  α-2,3-Sialyltransferase from <i>Neisseria </i><i>g</i><i>onorrheae</i>
  作者：Masayuki Izumi、Gwo-Jenn Shen、Shirley Wacowich-Sgarbi、Takuji Nakatani、Oliver Plettenburg、Chi-Huey Wong

  DOI：10.1021/ja011382r

  日期：2001.11.1

  exploitation of its substrate specificity and synthetic utility. Several potential acceptor substrates were synthesized in this study, including mono- and oligosaccharides, glycolipids, and glycopeptides and their sulfate derivatives. Some CMP-sialic acid derivatives with modification at the C-5 position were also prepared for evaluation as donor substrates. It was found that the enzyme exhibits a broader

  来自淋病奈瑟菌的 α-2,3-唾液酸转移酶在大肠杆菌中过度生产，以利用其底物特异性和合成效用。本研究合成了几种潜在的受体底物，包括单糖和寡糖、糖脂、糖肽及其硫酸盐衍生物。还制备了一些在 C-5 位进行修饰的 CMP-唾液酸衍生物作为供体底物进行评估。发现与其他唾液酸转移酶相比，该酶表现出更广泛的受体底物特异性，尽管供体特异性非常有限。已证明该酶在代表性唾液酸糖缀合物的制备性合成中的应用。在这项工作和其他人的工作的基础上，
• Synthesis of CMP-sialic acid conjugates: Substrates for the enzymatic synthesis of natural and designed sialyl oligosaccharides
  作者：Mark D. Chappell、Randall L. Halcomb

  DOI：10.1016/s0040-4020(97)00370-0

  日期：1997.8

  The syntheses of several congeners of CMP-NeuAc are described. These compounds are substrates for enzymatic glycosylation.

  描述了CMP-NeuAc的几种同源物的合成。这些化合物是酶促糖基化的底物。
• Studies on Sialic Acid. Part XXVII. Synthesis and Characterization of Furanose and Pyranose Derivatives of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN).
  作者：Mitsunobu NAKAMURA、Hiroaki TAKAYANAGI、Kimio FURUHATA、Haruo OGURA

  DOI：10.1248/cpb.40.879

  日期：——

  The products of Fischer's methyl glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) revealed existence of an the anomeric equilibrium between α, β-furanose and α, β-pyranose of KDN. In spite of the anomeric equilibrium, peracetylation of KDN and its derivatives by acetic anhydride with pyridine gave only α- and β-pyranose derivatives. The obtained methyl glycosides and hexa-O-acetyl derivatives were characterized by X-ray, nuclear magnetic resonance and cicular dichroism spectral analyses.

  3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)的费舍尔甲基糖基化产物表明，KDN 的 α, β-呋喃糖和 α, β-吡喃糖之间存在着异构体平衡。尽管存在同分异构平衡，但用乙酸酐与吡啶对 KDN 及其衍生物进行过乙酰化反应只能得到 α 和 β-吡喃糖衍生物。获得的甲基苷和六-O-乙酰基衍生物通过 X 射线、核磁共振和立体二色光谱分析进行了表征。