N-[5-(methyloxycarbonyl)pentyl]-1,5-dideoxy-1,5-imino-D-galactitol | 1240479-07-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-[5-(methyloxycarbonyl)pentyl]-1,5-dideoxy-1,5-imino-D-galactitol
• 英文别名: N-carboxypentyl-1-deoxy-D-galactonojirimycin；N-carboxypentyl-1,5-dideoxy-1,5-imino-D-galactitol；6-[(2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-ium-1-yl]hexanoate
• CAS: 1240479-07-5
• 化学式: C₁₂H₂₃NO₆
• 分子量: 277.318
• InChiKey: KTNVTDIFZTZBJY-LLHIFLOGSA-N

物化性质

• 熔点：
  >220°C (dec.)
• 沸点：
  534.3±50.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于甲醇（轻微加热）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  122
• 氢给体数：
  5
• 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 、 丹酰尸胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以267 mg的产率得到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 、 水 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 73.5h， 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.
• A fluorescent probe for GM1 gangliosidosis related β-galactosidase: N-(Dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-d-galactitol
  作者：Richard F.G. Fröhlich、Katrin Fantur、Richard H. Furneaux、Eduard Paschke、Arnold E. Stütz、Jacqueline Wicki、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.bmcl.2011.09.012

  日期：2011.11

  N-(Dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-galactitol, a strong competitive inhibitor of beta-galactosidase, enhances residual beta-galactosidase activities in fibroblasts and serves as lead en route to diagnostic compounds for tracking the fate of mutant beta-gal as well as aberrant GM1 gangliosides by live cell imaging. (C) 2011 Elsevier Ltd. All rights reserved.
• AFFINITY PURIFICATION OF GLYCOSIDE-CLEAVING ENZYMES
  申请人：SHIRE HUMAN GENETIC THERAPIES, INC.

  公开号：US20210040465A1

  公开（公告）日：2021-02-11

  The invention relates to an affinity resin functionalized with small molecule inhibitors of glycoside-cleaving enzymes, e.g., α-galactosidase A (α-Gal A), glucocerebrosidase (GCB), β-galactosidase, and acid alpha-glucosidase (GAA), and a method for purifying glycoside-cleaving enzymes produced in a cell line using the small molecule inhibitor-functionalized affinity resin.
• [EN] AFFINITY PURIFICATION OF GLYCOSIDE-CLEAVING ENZYMES<br/>[FR] PURIFICATION PAR AFFINITÉ D'ENZYMES DE CLIVAGE DE GLYCOSIDE
  申请人：SHIRE HUMAN GENETIC THERAPIES

  公开号：WO2019173293A1

  公开（公告）日：2019-09-12

  The invention relates to an affinity resin functionalized with small molecule inhibitors of glycoside-cleaving enzymes, e.g., a-galactosidase A (α-Gal A), glucocerebrosidase (GCB), β- galactosidase, and acid alpha-glucosidase (GAA), and a method for purifying glycoside-cleaving enzymes produced in a cell line using the small molecule inhibitor-functionalized affinity resin.
• 1-Deoxy-d-galactonojirimycins with dansyl capped N-substituents as β-galactosidase inhibitors and potential probes for GM1 gangliosidosis affected cell lines
  作者：Richard F.G. Fröhlich、Richard H. Furneaux、Don J. Mahuran、Robert Saf、Arnold E. Stütz、Michael B. Tropak、Jacqueline Wicki、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.carres.2011.05.010

  日期：2011.9

  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.