phenyl 2,3,4-p-methoxybenzyl-1-thio-β-D-galactopyranoside | 741677-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-p-methoxybenzyl-1-thio-β-D-galactopyranoside
• 英文别名: phenyl 2,3,4-tri-O-(4-methoxybenzyl)-6-hydroxy-1-thio-β-D-galactopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-tris[(4-methoxyphenyl)methoxy]-6-phenylsulfanyloxan-2-yl]methanol
• CAS: 741677-99-6
• 化学式: C₃₆H₄₀O₈S
• 分子量: 632.775
• InChiKey: DZTZWPAWXWIGIK-BVMCXEQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-p-methoxybenzyl-1-thio-β-D-galactopyranoside 在 吡啶 、 四氯化锡 、 sodium hydride 、 苯硫酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.83h， 生成 phenyl 2,3,4-tri-O-acetyl-6-O-(10-[2-naphthyl]-3,6,9-trioxadecanyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Rational Design, Synthesis, and Characterization of Novel Inhibitors for Human β1,4-Galactosyltransferase

  摘要：

  An affinity labeling reagent, uridine 5'-(6-amino-{2-[(7-bromomethyl-2-naphthyl)methoxy-carbonylmethoxy]ethoxy}acetyl-6-deoxy-alpha-D-galactopyranosyl) diphosphate (1a), was designed on the basis of 3D docking simulation and synthesized to investigate the functional role of Trp310 residue located in the small loop near the active site of human recombinant galactosyltransferase (beta GalT-1). Mass spectrometric analysis revealed that the Trp310 residue of beta GalT1 can be selectively modified with the naphthylmethyl group of compound la at the C-3 position of the indole ring. This result motivated us to synthesize novel uridine-5'-diphosphogalactose (UDP-Gal) analogues as candidates for mechanism-based inhibitors for beta GalT-1. We found that uridine 5'-(6-O-[10-(2-naphthyl)-3,6,9-trioxadecanyl]-alpha-D-galactopyranosyl) diphosphate (2) is the strongest inhibitor (K-i = 1.86 mu M) against UDP-Gal (K-m = 4.91 mu M) among compounds reported previously. A cold spray ionization time-of-flight mass spectrometry study demonstrated that the complex of this inhibitor and beta GalT-1 cannot interact with an acceptor substrate in the presence of Mn2+.

  DOI：

  10.1021/jm0504297
• 作为产物：
  描述：

  苯基-1-硫醇-beta-D-半乳糖苷 在 吡啶 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 32.83h， 生成 phenyl 2,3,4-p-methoxybenzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  靶向β-半乳糖苷酶的细胞渗透性双峰造影剂的合成与表征

  摘要：

  通过磁共振成像（MRI）对细胞内靶标（例如酶，受体或mRNA）的无创监测在各个研究领域中越来越重要。它们可视化的重要先决条件是细胞渗透性成像探针的开发，该探针可与表征目标细胞或分子过程的靶标特异性相互作用。在这里，我们描述了一种双标记探针Gd-DOTA-k（FR）-Gal-CPP，旨在通过MRI报告细胞内β-半乳糖苷酶（β-gal）酶的存在。这种结合物由半乳糖基核作为可裂解的间隔基，并掺入了穿透细胞的肽D-Tat 49-57之间和报道分子部分（Gd-DOTA，荧光素（FR））。我们采用了一种简便的构建模块方法来获得我们的双峰探针Gd-DOTA-k（FR）-Gal-CPP。该策略涉及使用Fmoc介导的固相合成制备结构单元并随后进行组装，然后使配体14与GdCl 3络合。的Gd-DOTA-K（FR）-Gal-CPP表现出显着更高的弛豫增强（16.8±0.6毫米-1 小号-1，123兆赫，~21℃）相对于市售的Gd-DOTA（4

  DOI：

  10.1016/j.bmc.2011.03.023

文献信息

• Rational Design, Synthesis, and Characterization of Novel Inhibitors for Human β1,4-Galactosyltransferase
  作者：Kenji Takaya、Noriko Nagahori、Masaki Kurogochi、Tetsuya Furuike、Nobuaki Miura、Kenji Monde、Yuan Chuan Lee、Shin-Ichiro Nishimura

  DOI：10.1021/jm0504297

  日期：2005.9.1

  An affinity labeling reagent, uridine 5'-(6-amino-2-[(7-bromomethyl-2-naphthyl)methoxy-carbonylmethoxy]ethoxy}acetyl-6-deoxy-alpha-D-galactopyranosyl) diphosphate (1a), was designed on the basis of 3D docking simulation and synthesized to investigate the functional role of Trp310 residue located in the small loop near the active site of human recombinant galactosyltransferase (beta GalT-1). Mass spectrometric analysis revealed that the Trp310 residue of beta GalT1 can be selectively modified with the naphthylmethyl group of compound la at the C-3 position of the indole ring. This result motivated us to synthesize novel uridine-5'-diphosphogalactose (UDP-Gal) analogues as candidates for mechanism-based inhibitors for beta GalT-1. We found that uridine 5'-(6-O-[10-(2-naphthyl)-3,6,9-trioxadecanyl]-alpha-D-galactopyranosyl) diphosphate (2) is the strongest inhibitor (K-i = 1.86 mu M) against UDP-Gal (K-m = 4.91 mu M) among compounds reported previously. A cold spray ionization time-of-flight mass spectrometry study demonstrated that the complex of this inhibitor and beta GalT-1 cannot interact with an acceptor substrate in the presence of Mn2+.
• Synthesis and characterization of a cell-permeable bimodal contrast agent targeting β-galactosidase
  作者：Aneta Keliris、Thomas Ziegler、Ritu Mishra、Rolf Pohmann、Martin G. Sauer、Kamil Ugurbil、Jörn Engelmann

  DOI：10.1016/j.bmc.2011.03.023

  日期：2011.4

  Noninvasive monitoring of intracellular targets such as enzymes, receptors, or mRNA by means of magnetic resonance imaging (MRI) is increasingly gaining relevance in various research areas. A vital prerequisite for their visualization is the development of cell-permeable imaging probes, which can specifically interact with the target that characterizes the cellular or molecular process of interest

  通过磁共振成像（MRI）对细胞内靶标（例如酶，受体或mRNA）的无创监测在各个研究领域中越来越重要。它们可视化的重要先决条件是细胞渗透性成像探针的开发，该探针可与表征目标细胞或分子过程的靶标特异性相互作用。在这里，我们描述了一种双标记探针Gd-DOTA-k（FR）-Gal-CPP，旨在通过MRI报告细胞内β-半乳糖苷酶（β-gal）酶的存在。这种结合物由半乳糖基核作为可裂解的间隔基，并掺入了穿透细胞的肽D-Tat 49-57之间和报道分子部分（Gd-DOTA，荧光素（FR））。我们采用了一种简便的构建模块方法来获得我们的双峰探针Gd-DOTA-k（FR）-Gal-CPP。该策略涉及使用Fmoc介导的固相合成制备结构单元并随后进行组装，然后使配体14与GdCl 3络合。的Gd-DOTA-K（FR）-Gal-CPP表现出显着更高的弛豫增强（16.8±0.6毫米-1 小号-1，123兆赫，~21℃）相对于市售的Gd-DOTA（4