β-1-C-methyl-deoxymannojirimycin | 125711-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: β-1-C-methyl-deoxymannojirimycin
• 英文别名: β-D-homofuconojirimycin；β-L-homofuconojirimycin；β-homofuconojirimycin；Beta-Homofuconojirimycin；(2R,3R,4R,5R,6S)-2-(hydroxymethyl)-6-methylpiperidine-3,4,5-triol
• CAS: 125711-55-9
• 化学式: C₇H₁₅NO₄
• 分子量: 177.2
• InChiKey: ZEWFPWKROPWRKE-CQOGJGKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-1-C-methyl-deoxymannojirimycin 在 palladium dihydroxide 氢气 、 sodium hydride 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， -50.0~25.0 ℃ 、379.21 kPa 条件下， 反应 25.08h， 生成 (2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine
  参考文献：
  名称：

  Synergistic Inhibition of Human α-1,3-Fucosyltransferase V

  摘要：

  Human alpha-1,3-fucosyltransferase V (FucT V), which catalyzes the transfer of L-fucose moiety from guanosine diphosphate beta-L-fucose (GDP-Fuc) to an acceptor sugar To form sialyl Lewis x (sLe(x)), was shown to proceed through an ordered, sequential mechanism by product inhibition studies. The designed azatrisaccharide propyl 2-acetamido-2-deoxy-4-O-(beta-D-galactopyranosyl)-3 -O-(2-(N-(beta-L-homofuconojirimycinyl))ethyl)-alpha-D- glucopyranoside (2), prepared by covalently linking the N-group of beta-L-homofuconojirimycin (1) to the 3-OH of LacNAc through an ethylene unit, in the presence of GDP was found to be an effective inhibitor of FucT V. In the presence of 30 mu M GDP, the concentration of 2 necessary to cause 50% inhibition was reduced 77-fold to 31 mu M. Presumably, the azatrisaccharide and GDP form a complex which mimics the transition state of the enzymatic reaction. Given the low affinity of FucT V for its substrate LacNAc (K-m = 35 mM), the designed azatrisaccharide in the presence of GDP represents the most potent synergistic inhibitor complex reported so far.

  DOI：

  10.1021/ja960274f
• 作为产物：
  描述：

  (3S,4S,5R)-5-[(1R)-1-azido-2-tert-butyldimethylsilanyloxyethyl]-3,4-isopropylidenedioxytetrahydrofuran-2-one 在 platinum(IV) oxide 氢气 作用下， 生成 β-1-C-methyl-deoxymannojirimycin
  参考文献：
  名称：

  Iminoheptitols as glycosidase inhibitors: synthesis of and specific α-L-fucosidase inhibition by β-L-homofuconojirimycin and 1-β-C-substituted deoxymannojirimycins

  摘要：

  DOI：

  10.1016/s0040-4039(00)99383-3

文献信息

• Synthesis of Azasugars through a Proline-Catalyzed Reaction
  作者：Félix Calderón、Elisa G. Doyagüez、Alfonso Fernández-Mayoralas

  DOI：10.1021/jo060568b

  日期：2006.8.1

  We report an efficient route to obtain azasugars from the enantiomerically pure l- and d-diethyltartrate. The key step is a proline-catalyzed aldol condensation, in which both enantiomers of proline have been used as catalyst, affording complementary anti-aldol products.

  我们报道了从对映体纯的l-和d-酒石酸二乙酯中获得氮杂糖的有效途径。关键步骤是脯氨酸催化的醛醇缩合，其中脯氨酸的两种对映异构体均已用作催化剂，从而提供了互补的抗醛醇缩合物。
• Rapid Diversity-Oriented Synthesis in Microtiter Plates for In Situ Screening: Discovery of Potent and Selectiveα-Fucosidase Inhibitors
  作者：Chung-Yi Wu、Chuan-Fa Chang、Jenny Szu-Yu Chen、Chi-Huey Wong、Chun-Hung Lin

  DOI：10.1002/anie.200351823

  日期：2003.10.6
• FLEET, G. W. J.;NAMGOONG, S. K.;BARKER, C.;BAINES, S.;JACOB, G. S.;WINCHE+, TETRAHEDRON LETT. , 30,(1989) N3, C. 4439-4442
  作者：FLEET, G. W. J.、NAMGOONG, S. K.、BARKER, C.、BAINES, S.、JACOB, G. S.、WINCHE+

  DOI：——

  日期：——
• Iminoheptitols as glycosidase inhibitors: synthesis of and specific α-L-fucosidase inhibition by β-L-homofuconojirimycin and 1-β-C-substituted deoxymannojirimycins
  作者：G.W.J. Fleet、S.K. Namgoong、C. Barker、S. Baines、G.S. Jacob、B. Winchester

  DOI：10.1016/s0040-4039(00)99383-3

  日期：1989.1
• Synergistic Inhibition of Human α-1,3-Fucosyltransferase V
  作者：Lei Qiao、Brion W. Murray、Makoto Shimazaki、Jody Schultz、Chi-Huey Wong

  DOI：10.1021/ja960274f

  日期：1996.1.1

  Human alpha-1,3-fucosyltransferase V (FucT V), which catalyzes the transfer of L-fucose moiety from guanosine diphosphate beta-L-fucose (GDP-Fuc) to an acceptor sugar To form sialyl Lewis x (sLe(x)), was shown to proceed through an ordered, sequential mechanism by product inhibition studies. The designed azatrisaccharide propyl 2-acetamido-2-deoxy-4-O-(beta-D-galactopyranosyl)-3 -O-(2-(N-(beta-L-homofuconojirimycinyl))ethyl)-alpha-D- glucopyranoside (2), prepared by covalently linking the N-group of beta-L-homofuconojirimycin (1) to the 3-OH of LacNAc through an ethylene unit, in the presence of GDP was found to be an effective inhibitor of FucT V. In the presence of 30 mu M GDP, the concentration of 2 necessary to cause 50% inhibition was reduced 77-fold to 31 mu M. Presumably, the azatrisaccharide and GDP form a complex which mimics the transition state of the enzymatic reaction. Given the low affinity of FucT V for its substrate LacNAc (K-m = 35 mM), the designed azatrisaccharide in the presence of GDP represents the most potent synergistic inhibitor complex reported so far.