(2R,3R,4S,5S,6R)-2-(2-苯基乙氧基)-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇 | 129932-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3R,4S,5S,6R)-2-(2-苯基乙氧基)-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
• 英文名称: 2-phenylethyl β-primeveroside
• 英文别名: phenethyl alcohol β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside；phenethyl alcohol β-D-xylopyranosyl(1->6)-β-D-glucopyranoside；2-phenylethyl O-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside；phenethyl alcohol β-D-xylopyranosyl(1→6)-β-D-glucopyranoside；phenethylalcohol β-D-xylopyranosyl(1→6)-β-D-glucopyranoside；2-phenylethyl β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside；2-Phenylethyl beta-primeveroside；(2R,3R,4S,5S,6R)-2-(2-phenylethoxy)-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• CAS: 129932-48-5
• 化学式: C₁₉H₂₈O₁₀
• 分子量: 416.425
• InChiKey: ZRGXCWYRIBRSQA-BMVMOQKNSA-N

物化性质

• 沸点：
  661.3±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6R)-2-(2-苯基乙氧基)-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇 在 β-primeverosidase 作用下， 以 various solvent(s) 为溶剂， 生成 primeverose
  参考文献：
  名称：

  Expression and Biochemical Characterization of β-Primeverosidase and Application of β-Primeverosylamidine to Affinity Purification

  摘要：

  β-Primeverosidase（PD）是一种家族1糖苷酶，催化β-早春花苷（6-O-β-d-木糖吡喃糖基-β-d-葡萄吡喃糖苷）水解，释放出早春花二糖。为了研究PD如何识别β-早春花苷的二糖部分，我们通过杆状病毒-昆虫细胞系统表达了重组PD。重组PD从High Five细胞中分泌出来，并进行了N-糖基化修饰和N端信号肽的正确切割。重组PD对β-早春花苷的糖苷部分表现出高度的底物特异性，与茶树中天然PD的底物特异性一致。接下来，合成了β-糖苷酰胺作为底物类似物抑制剂。β-早春花苷酰胺强烈抑制PD活性，而β-葡萄糖苷酰胺没有抑制作用。因此，β-早春花苷酰胺是一个理想的化学工具，用于探测PD活性位点中二糖的识别。使用β-早春花苷酰胺作为配体制备了PD的亲和吸附剂。亲和层析获得了高纯度的大量PD，允许进行晶体学研究。

  DOI：

  10.1271/bbb.70447
• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-α-D-xylopyranosyl bromide 在 sodium methylate 、 氰化汞 、 溴化钛(IV) 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 22.0h， 生成 (2R,3R,4S,5S,6R)-2-(2-苯基乙氧基)-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇
  参考文献：
  名称：

  The Role of Diglycosides as Tea Aroma Precursors:  Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves

  摘要：

  Two general synthetic routes were established in order to synthesize two diglycosides, primeverosides (1) and vicianosides (2), found in tea leaves. Procedure 1 is based on the Koenig-Knorr type of condensation of aglycon alcohols and 1-alpha-bromohexabenzoylprimeverose (6) and is suitable for the condensation of primary alcohols. Procedure 2 is to combine tribenzoyl-beta-D-glucoside (8) and 1-alpha-bromotribenzoylxylose (4). The primeveroside of a tertiary alcohol was synthesized by this method which is also applicable to the synthesis of vicianosides. The hydrolysis rate of each of the 12 synthesized glycosides by a crude tea enzyme was evaluated, which suggest that the main glycosidase is primeverosidase and the enzyme mixture shows substrate specificity to both the carbohydrate and aglycon moieties.

  DOI：

  10.1021/jf960852b

文献信息

• Substrate Specificity of β-Primeverosidase, A Key Enzyme in Aroma Formation during Oolong Tea and Black Tea Manufacturing
  作者：Seung-Jin MA、Masaharu MIZUTANI、Jun HIRATAKE、Kentaro HAYASHI、Kensuke YAGI、Naoharu WATANABE、Kanzo SAKATA

  DOI：10.1271/bbb.65.2719

  日期：2001.1

  monoglycoside of 2-phenylethanol to investigate the substrate specificity of the purified beta-primeverosidase from fresh leaves of a tea cultivar (Camellia sinensis var. sinensis cv. Yabukita) in comparison with the apparent substrate specificity of the crude enzyme extract from tea leaves. The crude enzyme extract mainly showed beta-primeverosidase activity, although monoglycosidases activity was present

  我们合成了9种二糖苷和2-苯基乙醇单糖苷，以研究茶树种（Camellia sinensis var。sinensis cv。Yabukita）鲜叶中纯化的β-primeverosidase的底物特异性，并比较其表面底物特异性。茶叶中的粗酶提取物。粗酶提取物主要表现出β-primeverosidase活性，尽管在一定程度上存在单糖苷酶活性。纯化的β-primeverosidase对糖蛋白部分显示非常狭窄的底物特异性，尤其是对β-primeverosyl（6-O-β-D-吡喃吡喃糖基-β-D-葡萄糖基吡喃糖基）部分的特异性。这些酶会水解天然存在的二糖苷，例如β-primeveroside，β-vicianoside，β-acuminoside，β-龙胆苷和6-O-α-L-阿拉伯呋喃糖基-β-D-吡喃葡萄糖苷，但无法水解合成的非天然二糖苷。纯化的酶对2-苯乙基β-D-吡喃葡萄糖苷没有活性。该酶将
• Preparation of Tea Aroma Precursor Glycosides: An Efficient and Sustainable Approach via Chemical Glycosidation
  作者：Tianlu Li、Tong Li、Youqin Zhang、Richard R. Schmidt、Peng Peng

  DOI：10.1021/acs.jafc.1c07043

  日期：2022.2.23

  addition, the influence of molecular sieves was elucidated. With regard to these findings, the serious problem of the competing orthoester formation side reaction was successfully overcome with low catalyst loading (1 mol %) and the use of 5 Å molecular sieves, leading to the preparation of a variety of tea aroma precursor β-d-glucopyranosides and β-primeverosides on a gram scale in high yields in an economical

  茶香前体甙是植物来源的天然产物，具有很大的经济价值。然而，在过去的几十年中，这些糖苷的制备在很大程度上仍然被忽视。在此，我们报告了一种温和、高效且可持续的化学催化工艺，用于生产茶香气前体糖苷。在研究糖苷化过程中，发现催化剂在有利于不同反应途径的产物形成中起决定性作用；此外，阐明了分子筛的影响。关于这些发现，通过低催化剂负载量（1 mol %）和使用 5 Å 分子筛成功克服了竞争性原酸酯形成副反应的严重问题，从而制备了多种茶香气前体 β- d以经济的方式以克级高产量生产吡喃葡萄糖苷和 β-primeverosides。综上所述，目前的方法具有催化糖苷化的特点，采用无毒、低成本的催化剂，具有良好的绿色性和可持续性，有望实现茶香前体糖苷的工业化生产。
• Chemoenzymatic Synthesis of Naturally Occurring Phenethyl (1→6)-β-D-Glucopyranosides
  作者：Hiroyuki Akita、Eiji Kawahara、Miho Nishiuchi、Mikio Fujii、Keisuke Kato、Yoshiteru Ida

  DOI：10.3987/com-05-10383

  日期：——
• Efficient Synthesis of β‐Primeverosides as Aroma Precursors by Transglycosylation of β‐Diglycosidase from <i>Penicillium multicolor</i>
  作者：Kazutaka Tsuruhami、Shigeharu Mori、Kanzo Sakata、Satoshi Amarume、Shigetaka Saruwatari、Takeomi Murata、Taichi Usui

  DOI：10.1080/07328300500439413

  日期：2005.11.1

  The enzyme activity transferring a beta-primeverosyl unit was found from culture filtrates of Penicillium multicolor IAM7153 and was useful for synthesizing a series of beta-primeverosides via a beta-primeverosyl transfer reaction in an aqueous-organic biphasic system. With the acceptors benzyl alcohol, 2-phenylethanol, and ( Z )-3-hexenol, the enzyme induced the transfer products benzyl, 2-phenylethyl, and ( Z )-3-hexyl beta-primeverosides in high yields of 51% to 70% based on the donor added. When geraniol and eugenol were used as acceptors, the corresponding geranyl and eugenyl beta-primeverosides were obtained in lower yields of 8% to 12%. The enzyme was an excellent tool for producing naturally occurring beta-primeverosides on a mmol scale.
• Guo, Wenfei; Yamauchi, Kazuyo; Watanabe, Naoharu, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 5, p. 962 - 964
  作者：Guo, Wenfei、Yamauchi, Kazuyo、Watanabe, Naoharu、Usui, Taiichi、Luo, Shaojun、Sakata, Kanzo

  DOI：——

  日期：——