m-carboxyphenyl- β-D-glucopyranoside | 128323-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: m-carboxyphenyl- β-D-glucopyranoside
• 英文别名: 3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
• CAS: 128323-95-5
• 化学式: C₁₃H₁₆O₈
• 分子量: 300.265
• InChiKey: QQYZSFSXSYHYIW-BZNQNGANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  21
• 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：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  m-carboxyphenyl- β-D-glucopyranoside 在 C-terminally His₆-tagged Oryza sativa L. β-glucosidase OsTAGG2 作用下， 以 aq. acetate buffer 为溶剂， 反应 0.17h， 生成 葡萄糖
  参考文献：
  名称：

  Identification of Rice β-Glucosidase with High Hydrolytic Activity towards Salicylic Acid β-D-Glucoside

  摘要：

  beta-Glucosidases (EC 3.2.1.21) split beta-glucosidic linkages at the non-reducing end of glucosides and oligosaccharides to release beta-D-glucose. One of the important functions of plant beta-glucosidase is deglucosylation of inactive glucosides of phytohormones to regulate levels of active hormones. Tuberonic acid is a jasmonate-related compound that shows tuber-inducing activity in the potato. We have identified two enzymes, OsTAGG1 and OsTAGG2, that have hydrolytic activity towards tuberonic acid beta-D-glucoside in rice (Oryza sativa L.). The expression of OsTAGG2 is upregulated by wounding and by methyl jasmonate, suggesting that this isozyme is involved in responses to biotic stresses and wounding, but the physiological substrate of OsTAGG2 remains ambiguous. In this study, we produced recombinant OsTAGG2 in Pichia pastoris (rOsTAGG2P), and investigated its substrate specificity in detail. From 1 L of culture medium, 2.1 mg of purified recombinant enzyme was obtained by ammonium sulfate precipitation and Ni-chelating column chromatography. The specific activity of rOsTAGG2P (182 U/mg) was close to that of the native enzyme (171 U/mg), unlike recombinant OsTAGG2 produced in Escherichia coli, which had approximately 3-fold lower specific activity than the native enzyme. The optimum pH and temperature for rOsTAGG2P were pH 3.4 and 60 degrees C. After pH and heat treatments, the enzyme retained its original activity in a pH range of 3.4-9.8 and below 55 degrees C. Native OsTAGG2 and rOsTAGG2P showed 4.5-4.7-fold higher activities towards salicylic acid beta-D-glucoside, an inactive storage-form of salicylic acid, than towards tuberonic acid beta-D-glucoside (TAG), although OsTAGG2 was originally isolated from rice based on TAG-hydrolytic activity.

  DOI：

  10.1271/bbb.120889
• 作为产物：
  描述：

  间羟基苯甲酸 生成 m-carboxyphenyl- β-D-glucopyranoside
  参考文献：
  名称：

  马蹄莲细胞悬浮培养物对羟基苯甲酸异构体的葡萄糖基化

  摘要：

  摘要 马蹄莲的培养细胞在8 小时的滞后期后将外源性邻羟基苯甲酸转化为O-葡萄糖苷，在此期间苷元被细胞迅速吸收，部分排泄然后重新吸收。苷元向 o - O -β- d - 葡萄糖基苯甲酸的葡萄糖基化与葡萄糖基转移酶活性的诱导几乎同时开始，并且大约 78% 的苷元在 12 小时内转化为葡萄糖苷。另一方面，间-和对-羟基苯甲酸在给药后立即被葡萄糖基化，后者同时产生其O-葡萄糖苷和葡萄糖酯。抑制剂实验表明 70S 或 80S 核糖体可能参与异构羟基苯甲酸的葡萄糖基化。

  DOI：

  10.1016/0031-9422(90)80120-6

文献信息

• 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
• Helferich; Lutzmann, Justus Liebigs Annalen der Chemie, 1939, vol. 537, p. 11,17
  作者：Helferich、Lutzmann

  DOI：——

  日期：——
• Identification of Rice β-Glucosidase with High Hydrolytic Activity towards Salicylic Acid β-<scp>D</scp>-Glucoside
  作者：Nami HIMENO、Wataru SABURI、Shinji WAKUTA、Ryosuke TAKEDA、Hideyuki MATSUURA、Kensuke NABETA、Sompong SANSENYA、James R. KETUDAT CAIRNS、Haruhide MORI、Ryozo IMAI、Hirokazu MATSUI

  DOI：10.1271/bbb.120889

  日期：2013.5.23

  beta-Glucosidases (EC 3.2.1.21) split beta-glucosidic linkages at the non-reducing end of glucosides and oligosaccharides to release beta-D-glucose. One of the important functions of plant beta-glucosidase is deglucosylation of inactive glucosides of phytohormones to regulate levels of active hormones. Tuberonic acid is a jasmonate-related compound that shows tuber-inducing activity in the potato. We have identified two enzymes, OsTAGG1 and OsTAGG2, that have hydrolytic activity towards tuberonic acid beta-D-glucoside in rice (Oryza sativa L.). The expression of OsTAGG2 is upregulated by wounding and by methyl jasmonate, suggesting that this isozyme is involved in responses to biotic stresses and wounding, but the physiological substrate of OsTAGG2 remains ambiguous. In this study, we produced recombinant OsTAGG2 in Pichia pastoris (rOsTAGG2P), and investigated its substrate specificity in detail. From 1 L of culture medium, 2.1 mg of purified recombinant enzyme was obtained by ammonium sulfate precipitation and Ni-chelating column chromatography. The specific activity of rOsTAGG2P (182 U/mg) was close to that of the native enzyme (171 U/mg), unlike recombinant OsTAGG2 produced in Escherichia coli, which had approximately 3-fold lower specific activity than the native enzyme. The optimum pH and temperature for rOsTAGG2P were pH 3.4 and 60 degrees C. After pH and heat treatments, the enzyme retained its original activity in a pH range of 3.4-9.8 and below 55 degrees C. Native OsTAGG2 and rOsTAGG2P showed 4.5-4.7-fold higher activities towards salicylic acid beta-D-glucoside, an inactive storage-form of salicylic acid, than towards tuberonic acid beta-D-glucoside (TAG), although OsTAGG2 was originally isolated from rice based on TAG-hydrolytic activity.
• Glucosylation of isomeric hydroxybenzoic acids by cell suspension cultures of Mallotus japonicus
  作者：Shigeo Tanaka、Keiko Hayakawa、Yasuko Umetani、Mamoru Tabata

  DOI：10.1016/0031-9422(90)80120-6

  日期：1990.1

  Abstract Cultured cells of Mallotus japonicus converted exogenous o -hydroxybenzoic acid into its O -glucoside after a lag period of 8 hr during which time the aglycone was taken up rapidly by the cells, partly excreted and then re-absorbed. The glucosylation of the aglycone into o - O -β- d -glucosylbenzoic acid began almost simultaneously with the induction of glucosyltransferase activity, and ca

  摘要 马蹄莲的培养细胞在8 小时的滞后期后将外源性邻羟基苯甲酸转化为O-葡萄糖苷，在此期间苷元被细胞迅速吸收，部分排泄然后重新吸收。苷元向 o - O -β- d - 葡萄糖基苯甲酸的葡萄糖基化与葡萄糖基转移酶活性的诱导几乎同时开始，并且大约 78% 的苷元在 12 小时内转化为葡萄糖苷。另一方面，间-和对-羟基苯甲酸在给药后立即被葡萄糖基化，后者同时产生其O-葡萄糖苷和葡萄糖酯。抑制剂实验表明 70S 或 80S 核糖体可能参与异构羟基苯甲酸的葡萄糖基化。