4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside | 53643-14-4

• 物质功能分类: 生物化工 - 糖类化合物 - 寡糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside
• 英文别名: 4-methylcoumarin-7-yloxy tetra-N-acetyl-β-chitotetraoside；GlcNAc1-b-4GlcNAc1-b-4GlcNAc1-b-4GlcNAc1-b-4MU；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 53643-14-4
• 化学式: C₄₂H₆₀N₄O₂₃
• 分子量: 988.951
• InChiKey: FMZCALJGBTWBDB-BGWTZNANSA-N

物化性质

• 熔点：
  280-281°C dec.
• 溶解度：
  DMSO（稍微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -7.2
• 重原子数：
  69
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  399
• 氢给体数：
  13
• 氢受体数：
  23

安全信息

• 储存条件：
  Amber vial and refrigerator

反应信息

• 作为反应物：
  描述：

  4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside 在 2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖 、 hen eggwhite (HEW) lysozyme 、 水 作用下， 反应 2.0h， 生成 羟甲香豆素
  参考文献：
  名称：

  Hydrolysis of 4-methylumbelliferyl tetra-N-acetyl-.BETA.-chitotetraoside by lysozyme and its inhibition by N,N',N"-triacetylchitotriose.

  摘要：

  溶菌酶对4-甲基伞形酮四-N-乙酰-β-壳四糖(4-MU-(GlcNAc)4)的水解活性受离子强度的影响很小,尽管溶菌酶对微球菌悬浮液的水解活性随离子强度的变化而有显著差异。0.1mM的N, N', N"-三乙酰壳三糖((GlcNAc)3)抑制了溶菌酶对4-MU-(GlcNAc)4作为底物的40-60%活性,但溶菌酶对微球菌的溶解活性影响不大。研究了鸡蛋清(HEW)溶菌酶和人胎盘(HP)溶菌酶对4-MU-(GlcNAc)4的水解动力学以及(GlcNAc)3对此水解的抑制作用。HEW溶菌酶和HP溶菌酶对4-MU-(GlcNAc)4的K5值分别为19.7μM和27.9μM,而Vmax值分别为0.124和0.0833 nmol/min/mg。两种酶的k值都很低,暗示底物分子中的切割键相对于溶菌酶活性位点的取向不佳。(GlcNAc)3以双曲线混合型抑制作用抑制溶菌酶。抑制作用降低了两种溶菌酶的Vmax值。加入抑制剂后,HEW溶菌酶的K5值增加,而HP溶菌酶的K5值降低。HEW溶菌酶和HP溶菌酶的Ki值分别为29.6μM和106μM。

  DOI：

  10.1248/cpb.32.3607
• 作为产物：
  描述：

  chitotetraose tetradecaacetate 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 氯仿 、 乙酸酐 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.17h， 生成 4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside
  参考文献：
  名称：

  Inaba, Toyoaki; Ohgushi, Tadayasu; Iga, Yoshiro, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1597 - 1603

  摘要：

  DOI：

文献信息

• Inaba, Toyoaki; Ohgushi, Tadayasu; Iga, Yoshiro, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1597 - 1603
  作者：Inaba, Toyoaki、Ohgushi, Tadayasu、Iga, Yoshiro、Hasegawa, Eiichi

  DOI：——

  日期：——
• Hydrolysis of 4-methylumbelliferyl tetra-N-acetyl-.BETA.-chitotetraoside by lysozyme and its inhibition by N,N',N"-triacetylchitotriose.
  作者：TSUYOSHI TANIMOTO、HIDEO FUKUDA、JIRO KAWAMURA

  DOI：10.1248/cpb.32.3607

  日期：——

  The hydrolytic activity of lysozyme towards 4-methylumbelliferyl tetra-N-acetyl-β-chitotetraoside (4-MU-(GlcNAc)4) was little affected by ionic strength, though the activity of lysozyme towards cell suspension of Micrococcus lysodeikticus varied markedly with ionic strength. About 40-60% of lysozyme activity with 4-MU-(GlcNAc)4 as a substrate was inhibited by 0.1mM N, N', N"-triacetylchitotriose ((GlcNAc)3), but the lytic activity of lysozyme towards M. lysodeikticus was little affected. The kinetics of hydrolysis of 4-MU-(GlcNAc)4 by hen egg-white (HEW) lysozyme and human placental (HP) lysozyme and the inhibition of this hydrolysis by (GlcNAc)3 were investigated. The K5 values for 4-MU-(GlcNAc)4 of HEW-and HP-lysozymes were 19.7 and 27.9μM, respectively, and the Vmax values were 0.124 and 0.0833 nmol/min/mg, respectively. The k values of both enzymes were very low, implying a poor orientation of the scissile bond in the substrate molecule with respect to the active site of lysozyme. (GlcNAc)3 inhibited lysozyme with hyperbolic mixed-type inhibition. The inhibition reduced the Vmax values of both lysozymes. The K5 value of HEW-lysozyme was increased by the addition of the inhibitor, whereas the K5 value of HP-lysozyme was decreased. The Ki value was 29.6μM for HEW-lysozyme and 106μM for HP-lysozyme.

  溶菌酶对4-甲基伞形酮四-N-乙酰-β-壳四糖(4-MU-(GlcNAc)4)的水解活性受离子强度的影响很小,尽管溶菌酶对微球菌悬浮液的水解活性随离子强度的变化而有显著差异。0.1mM的N, N', N"-三乙酰壳三糖((GlcNAc)3)抑制了溶菌酶对4-MU-(GlcNAc)4作为底物的40-60%活性,但溶菌酶对微球菌的溶解活性影响不大。研究了鸡蛋清(HEW)溶菌酶和人胎盘(HP)溶菌酶对4-MU-(GlcNAc)4的水解动力学以及(GlcNAc)3对此水解的抑制作用。HEW溶菌酶和HP溶菌酶对4-MU-(GlcNAc)4的K5值分别为19.7μM和27.9μM,而Vmax值分别为0.124和0.0833 nmol/min/mg。两种酶的k值都很低,暗示底物分子中的切割键相对于溶菌酶活性位点的取向不佳。(GlcNAc)3以双曲线混合型抑制作用抑制溶菌酶。抑制作用降低了两种溶菌酶的Vmax值。加入抑制剂后,HEW溶菌酶的K5值增加,而HP溶菌酶的K5值降低。HEW溶菌酶和HP溶菌酶的Ki值分别为29.6μM和106μM。