p-nitrophenyl 2-deoxy-α-D-arabino-hexopyranoside | 3650-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2-deoxy-α-D-arabino-hexopyranoside
• 英文别名: (4-nitro-phenyl)-(α-D-arabino-2-deoxy-hexopyranoside)；(4-Nitro-phenyl)-(α-D-arabino-2-desoxy-hexopyranosid)；p-Nitrophenyl-2-desoxy-α-D-glucosid；p-Nitrophenyl 2-deoxy-alpha-d-arabino-hexopyranoside；(2R,3S,4R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4-diol
• CAS: 3650-58-6
• 化学式: C₁₂H₁₅NO₇
• 分子量: 285.254
• InChiKey: GODNNWHTRQKNAC-WYUUTHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2-deoxy-α-D-arabino-hexopyranoside 在 potassium phosphate buffer 、 乙二胺四乙酸 、 rat liver microsomes 作用下， 生成 2-Deoxy-D-glucose
  参考文献：
  名称：

  Recognition Properties of Processing α‐Glucosidase I and α‐Glucosidase II

  摘要：

  All four possible monodeoxy derivatives of p-nitrophenyl alpha-D-glucopyranoside (PNP Glc) and 1-amino-2,6-anhydro-1-deOXY-D-glycero-D-ido-heptitol derivatives were prepared and used as substrates and inhibitors of rat liver processing alpha-glucosidases. alpha-Glucosidase II hydrolyzed the 2-deoxy derivative of PNP Glc (1); the hydrolysis of 1 was more rapid than that of PNP Glc. These results indicate that the presence of a C-2 hydroxyl group is not essential for the action of alpha-glucosidase II. In contrast, PNP Glc and all of the deoxy derivatives of PNP Glc 1-4 inhibited alpha-glucosidase I. These results indicate that alpha-glucosidase I does not necessarily need all of the hydroxyl groups of the glycon moiety for binding to the enzyme. 2,6-Anhydro-1-benzamide-D-glycero-D-ido-heptitol (11), with a terminal phenyl group, inhibited a-glucosidase I and a-glucosidase II. Both alpha-glucosidase I and II showed the same aglycon specificities. When probes 5-12 were assayed for their ability to inhibit processing by a-glucosidases at the cellular level, no effects on glycoprotein processing were observed.

  DOI：

  10.1081/car-120030022
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 21.0h， 生成 p-nitrophenyl 2-deoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Hydrolytic Activity ofα-Mannosidase against Deoxy Derivatives ofp-Nitrophenylα-d-Mannopyranoside

  摘要：

  合成了对硝基苯（PNP）α-d-吡喃甘露糖苷的脱氧衍生物、PNP 2-脱氧-α-d-阿拉伯诺-吡喃己糖苷、3-脱氧-α-d-阿拉伯诺-吡喃己糖苷、4-脱氧-α-d-来苏诺-吡喃己糖苷和α-d-鼠李糖苷，并研究了千层豆和杏仁α-甘露糖苷酶对它们的水解活性。这些α-甘露糖苷酶几乎不作用于 2-、3-和 4-脱氧衍生物，而 6-脱氧衍生物被酶水解的速度与 PNP α-d-吡喃甘露糖苷一样快，后者是α-甘露糖苷酶的常见底物。这些结果表明，曼吡喃糖苷的 C-2、3 和 4 处的羟基是这些酶识别底物的必要条件，而 C-6 处的羟基在底物鉴别中并没有如此关键的作用。动力学研究得出了酶水解 PNP α-d-rhamnopyranoside 的 Km 值和 Vmax 值。

  DOI：

  10.1271/bbb.60.2038

文献信息

• Glycosidase-catalyzed Deoxy Oligosaccharide Synthesis. Practical Synthesis of Monodeoxy Analogs of Ethyl β-Thioisomaltoside Using<i>Aspergillus niger</i>α-Glucosidase
  作者：Toshiyuki NISHIO、Chika KANAI、Wataru HAKAMATA、Masahiro OGAWA、Kousuke NAKAJIMA、Shigeki HOSHINO、Akari MATSUISHI、Ryu KAWACHI、Tadatake OKU

  DOI：10.1271/bbb.67.1024

  日期：2003.1

  Enzymatic transglycosylation using four possible monodeoxy analogs of p-nitrophenyl α-D-glucopyranoside (Glcα-O-pNP), modified at the C-2, C-3, C-4, and C-6 positions (2D-, 3D-, 4D-, and 6D-Glcα-O-pNP, respectively), as glycosyl donors and six equivalents of ethyl β-D-thioglucopyranoside (Glcβ-S-Et) as a glycosyl acceptor, to yield the monodeoxy derivatives of glucooligosaccharides were done. The reaction was catalyzed using purified Aspergillus niger α-glucosidase in a mixture of 50 mM sodium acetate buffer (pH 4.0)/CH3CN (1: 1 v/v) at 37°C. High activity of the enzyme was observed in the reaction between 2D-Glcα-O-pNP and Glcβ-S-Et to afford the monodeoxy analogs of ethyl β-thiomaltoside and ethyl β-thioisomaltoside that contain a 2-deoxy α-D-glucopyranose moiety at their glycon portions, namely ethyl 2-deoxy-α-D-arabino-hexopyranosyl-(1,4)-β-D-thioglucopyranoside and ethyl 2-deoxy-α-D-arabino-hexopyranosyl-(1,6)-β-D-thioglucopyranoside, in 6.72% and 46.6% isolated yields (based on 2D-Glcα-O-pNP), respectively. Moreover, from 3D-Glcα-O-pNP and Glcβ-S-Et, the enzyme also catalyzed the synthesis of the 3-deoxy analog of ethyl β-thioisomaltoside that was modified at the glycon α-D-glucopyranose moiety, namely ethyl 3-deoxy-α-D-ribo-hexopyranosyl-(1,6)-β-D-thioglucopyranoside, in 23.0% isolated yield (based on 3D-Glcα-O-pNP). Products were not obtained from the enzymatic reactions between 4D- or 6D-Glcα-O-pNP and Glcβ-S-Et.

  使用对硝基苯α-D-吡喃葡萄糖苷（Glcα-O-pNP）的四种可能的单脱氧类似物（分别在 C-2、C-3、C-4 和 C-6 位置进行修饰）（2D-、3D-、4D- 和 6D-Glcα-O-pNP）作为糖基供体，以及六种等量的乙基β-D-硫代吡喃葡萄糖苷（Glcβ-S-Et）作为糖基受体，进行酶促转糖基化、分别）作为糖基供体，六当量的乙基 β-D-硫代吡喃葡萄糖苷（Glcβ-S-Et）作为糖基受体，生成葡萄糖寡糖的单脱氧衍生物。该反应是在 50 mM 醋酸钠缓冲液（pH 4.0）/CH3CN（1: 1 v/v）的混合物中，于 37°C 下使用纯化的黑曲霉 α-葡萄糖苷酶催化的。在 2D-Glcα-O-pNP 和 Glcβ-S-Et 的反应中观察到该酶的高活性，从而得到乙基 β-硫代异麦芽糖苷和乙基 β-硫代异麦芽糖苷的单脱氧类似物、即乙基 2-脱氧-α-D-阿拉伯-六吡喃糖基-(1,4)-β-D-硫代吡喃葡萄糖苷和乙基 2-脱氧-α-D-阿拉伯-六吡喃糖基-(1,6)-β-D-硫代吡喃葡萄糖苷，分离率分别为 6.72% 和 46.6% 的分离收率（基于 2D-Glcα-O-pNP ）。此外，从三维-Glcα-O-pNP 和 Glcβ-S-Et 中，该酶还催化合成了乙基 β-硫代异麦芽糖苷的 3-脱氧类似物，即乙基 3-脱氧-α-D-核糖基-己吡喃糖基-(1,6)-β-D-硫代吡喃葡萄糖苷，分离产率为 23.0%（基于三维-Glcα-O-pNP）。4D- 或 6D-Glcα-O-pNP 与 Glcβ-S-Et 的酶促反应没有得到产物。
• METHOD OF EXPRESSING GENETICALLY MODIFIED PROTEIN CARRYING SUGAR CHAIN HAVING SIALIC ACID ADDED THERETO IN INSECT CELLS
  申请人：Incorporated Administrative Agency, National Agriculture and Bio-Oriented Research Organization

  公开号：EP1437413A1

  公开（公告）日：2004-07-14

  Provided is a method of expressing a recombinant protein having sialic acid added thereto in insect cells, which is advantageous in administration to animals. In this method, a recombinant protein carrying a sugar chain having sialic acid added thereto is expressed in an insect or insect cells, including suppressing, inhibiting or eliminating N-acetylglucosaminidase activity inherent in the insect cells.

  本发明提供了一种在昆虫细胞中表达添加了硅铝糖苷酸的重组蛋白的方法，该方法有利于给动物用药。在该方法中，在昆虫或昆虫细胞中表达携带有添加有硅铝酸的糖链的重组蛋白，包括抑制、抑制或消除昆虫细胞中固有的 N-乙酰葡糖苷酶活性。
• Method of expressing genetically modified protein carrying sugar chain having sialic acid added thereto in insect cells
  申请人：——

  公开号：US20040203117A1

  公开（公告）日：2004-10-14

  Provided is a method of expressing a recombinant protein having sialic acid added thereto in insect cells, which is advantageous in administration to animals. In this method, a recombinant protein carrying a sugar chain having sialic acid added thereto is expressed in an insect or insect cells, including suppressing, inhibiting or eliminating N-acetylglucosaminidase activity inherent in the insect cells.

  本发明提供了一种在昆虫细胞中表达添加了硅铝糖苷酸的重组蛋白的方法，该方法有利于给动物用药。在该方法中，在昆虫或昆虫细胞中表达携带有添加有硅铝酸的糖链的重组蛋白，包括抑制、抑制或消除昆虫细胞中固有的 N-乙酰葡糖苷酶活性。
• 926. The preparation and properties of aryl 2-deozy-α-<scp>D</scp>-glucopyranosides
  作者：F. Shafizadeh、M. Stacey

  DOI：10.1039/jr9570004612

  日期：——
• Glycon specificity profiling of α-glucosidases using monodeoxy and mono-O-methyl derivatives of p-nitrophenyl α-d-glucopyranoside
  作者：Toshiyuki Nishio、Wataru Hakamata、Atsuo Kimura、Seiya Chiba、Akira Takatsuki、Ryu Kawachi、Tadatake Oku

  DOI：10.1016/s0008-6215(02)00026-5

  日期：2002.4

  Hydrolysis of probe substrates, eight possible monodeoxy and mono-O-methyl analogs of p-nitrophenyl alpha-D-glucopyranoside (pNP alpha-D-Glc). modified at the C-2, C-3, C-4. and C-6 positions. was studied as part of investigations into the glycon specificities of seven alpha-glucosidases (EC 3.2.1.20) isolated from Saccharomyces cerevisiae, Bacillus stearothermophilus, honeybee (two enzymes). sugar beet, flint corn, and Aspergillus niger. The glucosidases from sugar beet, flint corn. and A. niger were found to hydrolyze the 2-deoxy analogs with substantially higher activities than against pNP alpha-D-Glc. Moreover, the flint corn and A. niger enzymes showed hydrolyzing activities, although low, for the 3-deoxy analog. The other four alpha-glucosidases did not exhibit any activities for either the 2- or the 3-deoxy analogs. None of the seven enzymes exhibited any activities toward the 4-deoxy, 6-deoxy, or any of the methoxy analogs. The hydrolysis results, with the deoxy substrate analogs, demonstrated that alpha-glucosidases having remarkably different glycon specificities exist in nature. Further insight into the hydrolysis of deoxyglycosides was obtained by determining the kinetic parameters (k(cat) and K-m) for the reactions of sugar beet, flint corn, and A. niger enzymes. (C) 2002 Elsevier Science Ltd. All rights reserved.