(3-nitro-2-pyridyl) β-D-galactopyranoside | 249928-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-nitro-2-pyridyl) β-D-galactopyranoside
• 英文别名: 3-nitro-2-pyridyl β-D-galactoside；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(3-nitropyridin-2-yl)oxyoxane-3,4,5-triol
• CAS: 249928-93-6
• 化学式: C₁₁H₁₄N₂O₈
• 分子量: 302.241
• InChiKey: UFROFMHPLNTAQY-YBEMZLNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3-nitro-2-pyridyl) β-D-galactopyranoside 在 β-D-galactosidase (Escherichia coli) 、 immobilized lipase (Amano PS) 作用下， 以 四氢呋喃 为溶剂， 反应 48.75h， 生成 [(2R,3R,4S,5R,6S)-6-[(3R,4R,5R,6S)-4,5-dihydroxy-6-(3-nitropyridin-2-yl)oxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  3-硝基-2-吡啶基糖苷作为化学糖基化的供体及其在寡糖化学酶法合成中的应用

  摘要：

  3-硝基-2-吡啶基（3NPy）糖苷在酶促糖基化反应中充当通用的糖基供体，也可以被化学活化。通过使用TMSOTf作为催化剂，在-20°C时很容易用保护的3NPy糖苷进行化学糖基化，以高收率提供所需的糖苷。三糖丝氨酸缀合物Gal（β1-3）Gal（β1-4）Xylβ-Ser是通过酶和化学糖基化的结合使用而合成的。通过使用β-半乳糖苷酶将Gal-3NPy供体逐步转糖基化为Xyl-3NPy受体来制备三糖3NPy糖苷。在通过乙酰化保护三糖的游离羟基之后，然后将3NPy糖苷进行丝氨酸残基的化学糖基化，得到三糖丝氨酸缀合物。

  DOI：

  10.1016/s0040-4039(99)01280-0
• 作为产物：
  描述：

  (3-nitro-2-pyridyl) 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 氨 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以100%的产率得到(3-nitro-2-pyridyl) β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and evaluation of glycosyl donors with novel leaving groups for transglycosylations employing β-galactosidase from bovine testes

  摘要：

  Novel aryl beta-D-galactopyranosides were synthesized employing phase-transfer catalysis, and assayed as potential galactose donors in the presence of P-galactosidase from bovine testes using pNP-Gal as a reference. The aglycones were represented mainly by nitrophenols containing halogens, hydroxymethyl, aldehyde, carboxyl, ester or amino functions. An unusual intermolecular acetyl migration onto the benzylic alcohol group was observed during galactosylation of hydroxymethylnitrophenols. Pyridyl glycosides were obtained by reaction with the corresponding silver pyridinolates. Glycosides of halo-, hydroxymethyl- or methoxy-carbonyl-nitrophenols as leaving groups gave virtually the same yields of transglycosylation products. A minor increase was achieved with nitrosalicylaldehyde as leaving group, whereas carboxy or amino derivatives gave very low or no yield of the transglycosylation product. Commercially available donors such as resorufinyl and 4-methylumbelliferyl beta-D-galactopyranosides exhibited a lower transglycosylation potential than these novel pNP-Gal derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.014

文献信息

• Nitropyridyl glycosides: new glycosyl donors for enzymatic transglycosylation
  作者：Takashi Yasukochi、Chikako Inaba、Koichi Fukase、Shoichi Kusumoto

  DOI：10.1016/s0040-4039(99)01279-4

  日期：1999.9

  New glycosyl donors, 3-nitro-2-pyridyl and 5-nitro-2-pyridyl glycosides, proved to be effective for transglycosylation reaction catalyzed by glycosidases, such as beta-galactosidase, B-glucosidase, and N-acetyl-beta-hexosaminidase. The high solubility in water and the high reactivity of the nitropyridyl glycosides enabled the reactions under high concentrations of the donors and consequently rapid glycosyl transfer to glycosyl accepters. The yields of the transglycosylated products with the nitropyridyl glycosides were much higher than those with conventional p-nitrophenyl glycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 3-Nitro-2-pyridyl glycoside as donor for chemical glycosylation and its application to chemoenzymatic synthesis of oligosaccharide
  作者：Takashi Yasukochi、Koichi Fukase、Shoichi Kusumoto

  DOI：10.1016/s0040-4039(99)01280-0

  日期：1999.9

  transglycosylation, can also be chemically activated. Chemical glycosylation with protected 3NPy glycosides was readily effected at −20°C by using TMSOTf as a catalyst to afford the desired glycosides in good yields. A trisaccharide serine conjugate Gal(β1-3)Gal(β1-4)Xylβ-Ser was synthesized by combined use of enzymatic and chemical glycosylations. The trisaccharide 3NPy glycoside was prepared by stepwise

  3-硝基-2-吡啶基（3NPy）糖苷在酶促糖基化反应中充当通用的糖基供体，也可以被化学活化。通过使用TMSOTf作为催化剂，在-20°C时很容易用保护的3NPy糖苷进行化学糖基化，以高收率提供所需的糖苷。三糖丝氨酸缀合物Gal（β1-3）Gal（β1-4）Xylβ-Ser是通过酶和化学糖基化的结合使用而合成的。通过使用β-半乳糖苷酶将Gal-3NPy供体逐步转糖基化为Xyl-3NPy受体来制备三糖3NPy糖苷。在通过乙酰化保护三糖的游离羟基之后，然后将3NPy糖苷进行丝氨酸残基的化学糖基化，得到三糖丝氨酸缀合物。
• Synthesis and evaluation of glycosyl donors with novel leaving groups for transglycosylations employing β-galactosidase from bovine testes
  作者：Lars Kröger、Joachim Thiem

  DOI：10.1016/j.carres.2006.10.014

  日期：2007.2

  Novel aryl beta-D-galactopyranosides were synthesized employing phase-transfer catalysis, and assayed as potential galactose donors in the presence of P-galactosidase from bovine testes using pNP-Gal as a reference. The aglycones were represented mainly by nitrophenols containing halogens, hydroxymethyl, aldehyde, carboxyl, ester or amino functions. An unusual intermolecular acetyl migration onto the benzylic alcohol group was observed during galactosylation of hydroxymethylnitrophenols. Pyridyl glycosides were obtained by reaction with the corresponding silver pyridinolates. Glycosides of halo-, hydroxymethyl- or methoxy-carbonyl-nitrophenols as leaving groups gave virtually the same yields of transglycosylation products. A minor increase was achieved with nitrosalicylaldehyde as leaving group, whereas carboxy or amino derivatives gave very low or no yield of the transglycosylation product. Commercially available donors such as resorufinyl and 4-methylumbelliferyl beta-D-galactopyranosides exhibited a lower transglycosylation potential than these novel pNP-Gal derivatives. (c) 2006 Elsevier Ltd. All rights reserved.