3-formylphenyl β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-formylphenyl β-D-glucopyranoside
• 英文别名: 3-β-D-glucopyranosyloxy-benzaldehyde；3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
• 化学式: C₁₃H₁₆O₇
• 分子量: 284.266
• InChiKey: MYKHRVYVTLUXGA-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-formylphenyl β-D-glucopyranoside 在 三氧化硫吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以39%的产率得到3-formylphenyl β-D-glucopyranoside-6-sulfate
  参考文献：
  名称：

  海藻糖6-磷酸磷酸酶可逆抑制剂的合理设计

  摘要：

  在某些生物中，环境压力触发了海藻糖生物合成，海藻糖生物合成由海藻糖6-磷酸合酶和海藻糖6-磷酸磷酸酶（T6PP）共同催化。T6PP催化将海藻糖6-磷酸酯（T6P）水解为海藻糖和无机磷酸酯，是开发抗菌，抗真菌和抗蠕虫药的有希望的目标。在这里，我们报告设计，合成和评估的芳基d-吡喃葡萄糖苷6硫酸盐的库，以用作小分子T6PP抑制剂的原型。稳态动力学技术用于测量一组源自病原体马来亚布鲁氏菌（Brugia malayi），猪scar虫（Ascaris suum），多种结构上不同的T6PP直系同源物的抑制常数（K i）。结核分枝杆菌，博伊氏志贺氏菌和鼠伤寒沙门氏菌。发现这些T6PP直系同源物中最活跃的抑制剂4-正辛基苯基α - d-吡喃葡萄糖苷6-硫酸盐（9a）的结合亲和力在低微摩尔范围内。与马来西亚芽孢杆菌T6PP直系同源物的9a的K i为5.3±0.6μM，比底物Michaelis常数小70倍。9

  DOI：

  10.1016/j.ejmech.2017.02.001
• 作为产物：
  描述：

  3-O-(2',3',4',6'-tetraacetyl-β-D-glucopyranosyloxy)-benzaldehyde 在 ammonium hydroxide 作用下， 生成 3-formylphenyl β-D-glucopyranoside
  参考文献：
  名称：

  Mauthner, Journal fur praktische Chemie (Leipzig 1954), 1931, vol. <2> 129, p. 278

  摘要：

  DOI：

文献信息

• COMPOSITIONS AND METHODS FOR IMMUNOTHERAPY
  申请人：BROWN Joe Ernest

  公开号：US20160008388A1

  公开（公告）日：2016-01-14

  The present invention provides novel immunotherapeutic compositions and methods useful for treating or preventing microbial infections, weakened immune systems, diseases in which cells have become obligately anerobic and cellular proliferative disorders including cancer. The immunotherapeutics herein use benzaldehyde derivatives, precursors and intermediaries alone or in combination with additional therapeutic agents to stimulate the immune system and inhibit cellular proliferation. The immunotherapeutics of the present invention are particularly useful in the treatment of microbial infections and cellular proliferative disorders which are resistant to traditional methods of treatment such as antibiotics and chemotherapy

  本发明提供了新型免疫治疗组合物和方法，可用于治疗或预防微生物感染、免疫系统衰弱、细胞成为厌氧菌和细胞增殖性疾病，包括癌症。本发明所述的免疫治疗剂使用苯甲醛衍生物、前体和中间体单独或与其他治疗剂联合使用，以刺激免疫系统并抑制细胞增殖。本发明的免疫治疗剂在治疗微生物感染和细胞增殖性疾病方面特别有用，这些疾病对传统的治疗方法如抗生素和化疗具有抵抗力。
• Diversification of phenolic glucosides by two UDP-glucosyltransferases featuring complementary regioselectivity
  作者：Fei Guo、Xingwang Zhang、Cai You、Chengjie Zhang、Fengwei Li、Nan Li、Yuwei Xia、Mingyu Liu、Zetian Qiu、Xianliang Zheng、Li Ma、Gang Zhang、Lianzhong Luo、Fei Cao、Yingang Feng、Guang-Rong Zhao、Wei Zhang、Shengying Li、Lei Du

  DOI：10.1186/s12934-022-01935-w

  日期：——

  pharmaceutical demands. Microbial synthetic biology offers promising strategies for synthesis and diversification of plant glycosides. In this study, the two efficient UDP-glucosyltransferases (UGTs) (UGT85A1 and RrUGT3) of plant origin, that are capable of recognizing phenolic aglycons, are characterized in vitro. The two UGTs show complementary regioselectivity towards the alcoholic and phenolic hydroxyl groups

  葡糖苷类天然产物已显示出巨大的药用价值和潜力。然而，通过植物提取、化学合成和传统的生物转化生产糖苷已不足以满足快速增长的制药需求。微生物合成生物学为植物苷的合成和多样化提供了有前景的策略。在这项研究中，能够识别酚苷配基的两种植物来源的高效 UDP-葡萄糖基转移酶 (UGT)（UGT85A1 和 RrUGT3）在体外进行了表征。两种 UGT 对酚类底物上的醇和酚羟基显示出互补的区域选择性。通过将开发的烷基酚生物氧化系统与这些 UGT 相结合，二十四种酚糖苷是由容易获得的烷基酚底物酶促合成的。基于生物氧化和糖基化系统，构建了多个微生物细胞工厂并将其应用于生物转化，产生了多种植物和类植物O-糖苷。值得注意的是，这两种UGTs制备的几种非天然O-糖苷表现出比临床使用的糖苷类药物包括天麻素、红景天苷和螺旋体更好的脯氨酰内肽酶抑制和/或抗炎活性。此外，这两种UGT还能够催化N-和S-糖苷键的形成以产生
• Compositions And Methods For Immunotherapy
  申请人：BROWN Joe Ernest

  公开号：US20090281047A1

  公开（公告）日：2009-11-12

  The present invention provides novel immunotherapeutic compositions and methods useful for treating or preventing microbial infections, weakened immune systems, diseases in which cells have become obligately anerobic and cellular proliferative disorders including cancer. The immunotherapeutics herein use benzaldehyde derivatives, precursors and intermediaries alone or in combination with additional therapeutic agents to stimulate the immune system and inhibit cellular proliferation. The immunotherapeutics of the present invention are particularly useful in the treatment of microbial infections and cellular proliferative disorders which are resistant to traditional methods of treatment such as antibiotics and chemotherapy
• Infusion Treatment Methods And Compositions Using Salicinium For Treating Cellular Proliferative Disorders And Immune Deficiencies
  申请人：Brown Joe Ernest

  公开号：US20110311477A1

  公开（公告）日：2011-12-22

  The present invention provides novel immunotherapeutic compositions and methods useful for treating or preventing microbial infections, weakened immune systems, diseases in which cells have become obligately anaerobic and cellular proliferative disorders including cancer. The immunotherapeutics herein use benzaldehyde derivatives, precursors and intermediaries alone or in combination with additional therapeutic agents to stimulate the immune system and inhibit cellular proliferation. The immunotherapeutics of the present invention are particularly useful in the treatment of microbial infections and cellular proliferative disorders which are resistant to traditional methods of treatment such as antibiotics and chemotherapy
• Methods For Treating An Immune Deficiency Or Enhancing Immune Function Using Salicinium, Non-Limited In Terms Of Treatment Indication, But Encompassing Methods For Treating Cancer And Microbial, Bacterial, Viral, Fungal; Non-Limited In Terms of Delivery Mode, Formulation
  申请人：BROWN Joe Ernest

  公开号：US20110311476A1

  公开（公告）日：2011-12-22

  The present invention provides novel immunotherapeutic compositions and methods useful for treating or preventing microbial infections, weakened immune systems, diseases in which cells have become obligately anaerobic and cellular proliferative disorders including cancer. The immunotherapeutics herein use benzaldehyde derivatives, precursors and intermediaries alone or in combination with additional therapeutic agents to stimulate the immune system and inhibit cellular proliferation. The immunotherapeutics of the present invention are particularly useful in the treatment of microbial infections and cellular proliferative disorders which are resistant to traditional methods of treatment such as antibiotics and chemotherapy