methyl 1,3-O-isopropylidene-6-O-tosyl-α-D-fructofuranoside | 870248-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 1,3-O-isopropylidene-6-O-tosyl-α-D-fructofuranoside
• 英文别名: [(4aS,6R,7R,7aS)-7-hydroxy-4a-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-6-yl]methyl 4-methylbenzenesulfonate
• CAS: 870248-43-4
• 化学式: C₁₇H₂₄O₈S
• 分子量: 388.439
• InChiKey: RPKNPSWIVVXUIA-AIANPOQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 1,3-O-isopropylidene-6-O-tosyl-α-D-fructofuranoside 在 sodium azide 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Fluorescent Hexose Conjugates Establish Stringent Stereochemical Requirement by GLUT5 for Recognition and Transport of Monosaccharides

  摘要：

  The specificity characteristics of transporters can be exploited for the development of novel diagnostic therapeutic probes. The facilitated hexose transporter family (GLUTs) has a distinct set of preferences for monosaccharide substrates, and while some are expressed ubiquitously (e.g., GLUT1), others are quite tissue specific,(e.g., GLUTS, which is overexpressed in some breast cancer tissues). While these differences have enabled the development of new molecular probes based upon hexose-and tissue-selective uptake, substrate design for compounds targeting these GLUT transporters has been encumbered by a limited understanding of the molecular interactions at play in hexose binding and transport. Four new fluorescently labeled hexose derivatives have been prepared, and their transport characteristics were examined in two breast cancer cell lines expressing mainly GLUTs 1, 2, and 5. Our results demonstrate, for the first time, a stringent stereochemical requirement for recognition and transport by GLUTS, 6-NBDF, in which all substituents are in the D-fructose configuration, is taken up rapidly into both cell lines via GLUTS. On the other hand, inversion of a single stereocenter at C-3 (6-NBDP), C-4 (6-NBDT), or C-5 (6-NDBS) results in selective transport via GLUT1. An in silico docking study employing the recently published GLUTS crystal structure confirms this stereochemical dependence. This work provides insight into hexose-GLUT interactions the molecular level and will facilitate structure-based design of novel substrates targeting individual members of the GLUT family and forms the basis of new cancer imaging or therapeutic agents.

  DOI：

  10.1021/acschembio.6b01101
• 作为产物：
  描述：

  D-fructose 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 40.67h， 生成 methyl 1,3-O-isopropylidene-6-O-tosyl-α-D-fructofuranoside
  参考文献：
  名称：

  Fluorescent Hexose Conjugates Establish Stringent Stereochemical Requirement by GLUT5 for Recognition and Transport of Monosaccharides

  摘要：

  The specificity characteristics of transporters can be exploited for the development of novel diagnostic therapeutic probes. The facilitated hexose transporter family (GLUTs) has a distinct set of preferences for monosaccharide substrates, and while some are expressed ubiquitously (e.g., GLUT1), others are quite tissue specific,(e.g., GLUTS, which is overexpressed in some breast cancer tissues). While these differences have enabled the development of new molecular probes based upon hexose-and tissue-selective uptake, substrate design for compounds targeting these GLUT transporters has been encumbered by a limited understanding of the molecular interactions at play in hexose binding and transport. Four new fluorescently labeled hexose derivatives have been prepared, and their transport characteristics were examined in two breast cancer cell lines expressing mainly GLUTs 1, 2, and 5. Our results demonstrate, for the first time, a stringent stereochemical requirement for recognition and transport by GLUTS, 6-NBDF, in which all substituents are in the D-fructose configuration, is taken up rapidly into both cell lines via GLUTS. On the other hand, inversion of a single stereocenter at C-3 (6-NBDP), C-4 (6-NBDT), or C-5 (6-NDBS) results in selective transport via GLUT1. An in silico docking study employing the recently published GLUTS crystal structure confirms this stereochemical dependence. This work provides insight into hexose-GLUT interactions the molecular level and will facilitate structure-based design of novel substrates targeting individual members of the GLUT family and forms the basis of new cancer imaging or therapeutic agents.

  DOI：

  10.1021/acschembio.6b01101

文献信息

• Facile synthesis of core intermediates toward sialyl nucleoside mimetics
  作者：Hyeok Beom Kwon、Mark von Itzstein、Kang-Yeoun Jung

  DOI：10.1016/j.tetlet.2009.03.050

  日期：2009.5

  6-Deoxyphosphonated intermediates, 8 and 12, were efficiently synthesized from D-fructose and sucrose, respectively. These novel intermediates will be useful to synthesize various D-tagato- and fructofuranoside derivatives as inhibitors of sialyl transferase or sialidase. (C) 2009 Elsevier Ltd. All rights reserved.
• An efficient synthesis of methyl 1,3-O-isopropylidene-α-d-fructofuranoside and 2,3:5,6-di-O-isopropylidene-d-glucose dimethyl acetal derivatives from sucrose
  作者：Tadashi Hanaya、Nobuaki Sato、Hiroshi Yamamoto

  DOI：10.1016/j.carres.2005.07.023

  日期：2005.11

  Acetalation of sucrose with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, followed by acetylation, afforded methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-alpha-D-fructofuranoside and 4-O-acetyl-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal as major products, while tosylation of the intermediate acetals provided methyl 6-O-tosyl-1,3-O-isopropytidene-alpha-D-fructofuranose. (C) 2005 Elsevier Ltd. All rights reserved.
• The First Chemical Synthesis of 6-Thio-D-fructopyranose via Methyl 6-Bromo-6-deoxy-1,3-O-isopropylidene-α-D-fructofuranoside as a Key Intermediate
  作者：Tadashi Hanaya、Nobuaki Sato、Hiroshi Yamamoto

  DOI：10.3987/com-06-10965

  日期：——

  Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-alpha-D-fructofuranoside (4). The first chemical synthesis of 6-thio-D-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.
• Fluorescent Hexose Conjugates Establish Stringent Stereochemical Requirement by GLUT5 for Recognition and Transport of Monosaccharides
  作者：Olivier-Mohamad Soueidan、Thomas W. Scully、Jatinder Kaur、Rashmi Panigrahi、Alexandr Belovodskiy、Victor Do、Carson D. Matier、M. Joanne Lemieux、Frank Wuest、Chris Cheeseman、F. G. West

  DOI：10.1021/acschembio.6b01101

  日期：2017.4.21

  The specificity characteristics of transporters can be exploited for the development of novel diagnostic therapeutic probes. The facilitated hexose transporter family (GLUTs) has a distinct set of preferences for monosaccharide substrates, and while some are expressed ubiquitously (e.g., GLUT1), others are quite tissue specific,(e.g., GLUTS, which is overexpressed in some breast cancer tissues). While these differences have enabled the development of new molecular probes based upon hexose-and tissue-selective uptake, substrate design for compounds targeting these GLUT transporters has been encumbered by a limited understanding of the molecular interactions at play in hexose binding and transport. Four new fluorescently labeled hexose derivatives have been prepared, and their transport characteristics were examined in two breast cancer cell lines expressing mainly GLUTs 1, 2, and 5. Our results demonstrate, for the first time, a stringent stereochemical requirement for recognition and transport by GLUTS, 6-NBDF, in which all substituents are in the D-fructose configuration, is taken up rapidly into both cell lines via GLUTS. On the other hand, inversion of a single stereocenter at C-3 (6-NBDP), C-4 (6-NBDT), or C-5 (6-NDBS) results in selective transport via GLUT1. An in silico docking study employing the recently published GLUTS crystal structure confirms this stereochemical dependence. This work provides insight into hexose-GLUT interactions the molecular level and will facilitate structure-based design of novel substrates targeting individual members of the GLUT family and forms the basis of new cancer imaging or therapeutic agents.