N-[5-(methyloxycarbonyl)pentyl]-1,5-dideoxy-1,5-imino-D-galactitol | 1320341-50-1

• 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: N-[5-(methyloxycarbonyl)pentyl]-1,5-dideoxy-1,5-imino-D-galactitol
• 英文别名: N-methoxycarbonylpentyl-1,5-dideoxy-1,5-imino-D-galactitol；N-methoxycarbonylpentyl-1-deoxy-D-galactonojirimycin；methyl 6-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]hexanoate
• CAS: 1320341-50-1
• 化学式: C₁₃H₂₅NO₆
• 分子量: 291.345
• InChiKey: WVUKAACIBVWUPR-RSLMWUCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[5-(methyloxycarbonyl)pentyl]-1,5-dideoxy-1,5-imino-D-galactitol 在 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-[(dansylamino)hexyl]aminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-galactitol
  参考文献：
  名称：

  1-Deoxy-d-galactonojirimycins with dansyl capped N-substituents as β-galactosidase inhibitors and potential probes for GM1 gangliosidosis affected cell lines

  摘要：

  Two simple and reliably accessible intermediates, N-carboxypentyl- and N-aminohexyl-1-deoxy-D-galactonojirimycin were employed for the synthesis of a set of terminally N-dansyl substituted derivatives. Reaction of the terminal carboxylic acid of N-carboxypentyl-1-deoxy-D-galactonojirimycin with N-dansyl-1,6-diaminohexane provided the chain-extended fluorescent derivative. Employing bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Partially protected N-aminohexyl-1-deoxy-D-galactonojirimycin served as intermediate for two additional chain-extended fluorescent 1-deoxy-D-galactonojirimycin (1-DGJ) derivatives featuring terminal dansyl groups in the N-alkyl substituent. These new compounds are strong inhibitors of D-galactosidases and may serve as leads en route to pharmacological chaperones for GM1-gangliosidosis. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2011.05.010
• 作为产物：
  描述：

  (6-甲氧基-6-氧代己基)胺 在 盐酸 、 甲醇 、 20% palladium(II) hydroxide on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 N-[5-(methyloxycarbonyl)pentyl]-1,5-dideoxy-1,5-imino-D-galactitol
  参考文献：
  名称：

  1-Deoxy-d-galactonojirimycins with dansyl capped N-substituents as β-galactosidase inhibitors and potential probes for GM1 gangliosidosis affected cell lines

  摘要：

  Two simple and reliably accessible intermediates, N-carboxypentyl- and N-aminohexyl-1-deoxy-D-galactonojirimycin were employed for the synthesis of a set of terminally N-dansyl substituted derivatives. Reaction of the terminal carboxylic acid of N-carboxypentyl-1-deoxy-D-galactonojirimycin with N-dansyl-1,6-diaminohexane provided the chain-extended fluorescent derivative. Employing bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Partially protected N-aminohexyl-1-deoxy-D-galactonojirimycin served as intermediate for two additional chain-extended fluorescent 1-deoxy-D-galactonojirimycin (1-DGJ) derivatives featuring terminal dansyl groups in the N-alkyl substituent. These new compounds are strong inhibitors of D-galactosidases and may serve as leads en route to pharmacological chaperones for GM1-gangliosidosis. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2011.05.010

文献信息

• Synthesis and biological evaluation of novel biotin–iminoalditol conjugates
  作者：Gerit Pototschnig、Christian Morales De Csáky、Jose R. Montenegro Burke、Georg Schitter、Arnold E. Stütz、Chris A. Tarling、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.bmcl.2010.05.084

  日期：2010.7

  Biotin-iminosugar conjugates of different configuration such as D-gluco, D-galacto, L-ido as well as a furanoid representative in the D-manno configuration have been synthesised and exhibit powerful inhibition of beta-glucosidase from Agrobacterium sp. with K(i) values in the range of the respective parent compounds. Such molecular probes have potential for activity-based protein pro. ling taking advantage of the biotin-(strept)avidin interaction. (C) 2010 Elsevier Ltd. All rights reserved.