propyl 2-acetamido-2-deoxy-α-D-glucopyranoside | 19124-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl 2-acetamido-2-deoxy-α-D-glucopyranoside
• 英文别名: Propyl-2-acetamino-2-deoxy-α-D-glucopyranosid；N-(O¹-propyl-α-D-glucopyranose-2-yl)-acetamide；N-(O¹-Propyl-α-D-glucopyranose-2-yl)-acetamid；N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-propoxyoxan-3-yl]acetamide
• CAS: 19124-39-1
• 化学式: C₁₁H₂₁NO₆
• 分子量: 263.291
• InChiKey: ZQKFRTNUONNUBH-ILAIQSSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  propyl 2-acetamido-2-deoxy-α-D-glucopyranoside 、 pNP 6-sulfo-β-D-GlcNAc sodium salt 在 Aspergillus oryzae N-acetylhexosaminidase 作用下， 以 phosphate buffer 为溶剂， 反应 144.0h， 以87%的产率得到sodium;N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-propoxyoxan-3-yl]oxy-4,5-dihydroxy-6-(sulfooxymethyl)oxan-3-yl]ethanimidate
  参考文献：
  名称：

  Substrate specificity of N-acetylhexosaminidase from Aspergillus oryzae to artificial glycosyl acceptors having various substituents at the reducing ends

  摘要：

  The substrate specificity of N-acetylhexosaminidase (E.C. 3.2.1.51) from Aspergillus oryzae was examined using p-nitrophenyl 6-O-sulfo-N-acetyl-beta-D-glucosaminide (6-O-sulfo-GlcNAc-O-pNP) as the glycosyl donor and a series of beta-D-glucopyranosides and N-acetyl-beta-D-glucosaminides with variable aglycons at the anomeric positions as the acceptors. When beta-D-glucopyranosides with methyl (CH3) allyl (CH2CH=CH2), and phenyl (C6H5) groups at the reducing end were used as the acceptors, this enzyme transferred the 6-O-sulfo-GlcNAc moiety in the donor to the location of O-4 in these glycosyl acceptors with a high regioselectivity, producing the corresponding 6-O-sulfo-N-acetylglucosaminyl beta-D-glucopyranosides. However, beta-D-glucopyranose lacking aglycon was a poor substrate for transglycosylation. This A. oryzae enzyme could also accept various N-acetyl-beta-D-glucosaminides carrying hydroxyl (OH), methyl (CH3) propyl (CH2CH2CH3), allyl (CH2CH=CH2) and p-nitrophenyl (PNP; C6H4-NO2) groups at their aglycons, yielding 6-O-sulfo-N-acetylglucosaminyl-beta(1 -> 4)-disaccharide products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.004
• 作为产物：
  描述：

  乙酸酐 、 propyl 2-amino-2-deoxy-α-D-glucopyranoside 以 甲醇 为溶剂， 反应 0.75h， 以84%的产率得到propyl 2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  N-乙酰氨基葡糖衍生物的化学合成及其作为中生根瘤菌甲壳质寡糖合酶NodC的糖基受体的用途

  摘要：

  摘要根瘤菌细菌合成了脂-几丁质寡糖信号分子（Nod因子），这对于在宿主植物根部形成共生器官至关重要，这一过程称为结瘤。Nod因子中的几丁质寡糖部分的生物合成是通过根瘤菌N-乙酰氨基葡萄糖氨基转移酶NodC进行的。用于体内几丁质寡糖合成的初始受体或引物是未知的。为了研究NodC的受体特异性，我们合成了具有不同糖苷配基的N-乙酰氨基葡糖（GlcNAc）衍生物，并使用表达lotorhizobium loti几丁质寡糖合酶NodC的大肠杆菌菌株的膜制剂在体外测试了它们是否为NodC的受体。使用薄层色谱法分析反应产物表明，含有简单烷基链或连接C-1的其他疏水基团的GlcNAc衍生物是NodC的受体。该酶似乎对糖苷配基是β-连接的受体具有特异性。NodC仍将其中GlcNAc的N-乙酰基部分的甲基被烯丙氧基或苄氧基取代的GlcNAc衍生物用作受体。因此，在该位置上的原始甲基对于NodC和GlcNAc之间

  DOI：

  10.1016/s0008-6215(99)00190-1

文献信息

• Zilliken et al., Archives of Biochemistry, 1955, vol. 54, p. 398,402
  作者：Zilliken et al.

  DOI：——

  日期：——
• Chemical synthesis of N-acetylglucosamine derivatives and their use as glycosyl acceptors by the Mesorhizobium loti chitin oligosaccharide synthase NodC
  作者：Eric Kamst、Korien Zegelaar-Jaarsveld、Gijs A. van der Marel、Jacques H. van Boom、Ben J.J. Lugtenberg、Herman P. Spaink

  DOI：10.1016/s0008-6215(99)00190-1

  日期：1999.10

  lipo-chitin oligosaccharide signal molecules (Nod factors) that are essential for the formation of symbiotic organs on the roots of host plants, a process known as nodulation. Biosynthesis of the chitin oligosaccharide moiety in Nod factors is carried out by the rhizobial N-acetylglucosaminyltransferase NodC. The initial acceptor or primer used for the synthesis of chitin oligosaccharides in vivo is

  摘要根瘤菌细菌合成了脂-几丁质寡糖信号分子（Nod因子），这对于在宿主植物根部形成共生器官至关重要，这一过程称为结瘤。Nod因子中的几丁质寡糖部分的生物合成是通过根瘤菌N-乙酰氨基葡萄糖氨基转移酶NodC进行的。用于体内几丁质寡糖合成的初始受体或引物是未知的。为了研究NodC的受体特异性，我们合成了具有不同糖苷配基的N-乙酰氨基葡糖（GlcNAc）衍生物，并使用表达lotorhizobium loti几丁质寡糖合酶NodC的大肠杆菌菌株的膜制剂在体外测试了它们是否为NodC的受体。使用薄层色谱法分析反应产物表明，含有简单烷基链或连接C-1的其他疏水基团的GlcNAc衍生物是NodC的受体。该酶似乎对糖苷配基是β-连接的受体具有特异性。NodC仍将其中GlcNAc的N-乙酰基部分的甲基被烯丙氧基或苄氧基取代的GlcNAc衍生物用作受体。因此，在该位置上的原始甲基对于NodC和GlcNAc之间
• Substrate specificity of N-acetylhexosaminidase from Aspergillus oryzae to artificial glycosyl acceptors having various substituents at the reducing ends
  作者：Makoto Ogata、Xiaoxiong Zeng、Taichi Usui、Hirotaka Uzawa

  DOI：10.1016/j.carres.2006.11.004

  日期：2007.1

  The substrate specificity of N-acetylhexosaminidase (E.C. 3.2.1.51) from Aspergillus oryzae was examined using p-nitrophenyl 6-O-sulfo-N-acetyl-beta-D-glucosaminide (6-O-sulfo-GlcNAc-O-pNP) as the glycosyl donor and a series of beta-D-glucopyranosides and N-acetyl-beta-D-glucosaminides with variable aglycons at the anomeric positions as the acceptors. When beta-D-glucopyranosides with methyl (CH3) allyl (CH2CH=CH2), and phenyl (C6H5) groups at the reducing end were used as the acceptors, this enzyme transferred the 6-O-sulfo-GlcNAc moiety in the donor to the location of O-4 in these glycosyl acceptors with a high regioselectivity, producing the corresponding 6-O-sulfo-N-acetylglucosaminyl beta-D-glucopyranosides. However, beta-D-glucopyranose lacking aglycon was a poor substrate for transglycosylation. This A. oryzae enzyme could also accept various N-acetyl-beta-D-glucosaminides carrying hydroxyl (OH), methyl (CH3) propyl (CH2CH2CH3), allyl (CH2CH=CH2) and p-nitrophenyl (PNP; C6H4-NO2) groups at their aglycons, yielding 6-O-sulfo-N-acetylglucosaminyl-beta(1 -> 4)-disaccharide products. (c) 2006 Elsevier Ltd. All rights reserved.