(S)-1-phenylethyl β-D-glucopyranoside | 74284-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-phenylethyl β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(1S)-1-phenylethoxy]oxane-3,4,5-triol
• CAS: 74284-26-7
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: FVJSVPNFQKQHOB-VWJSEBMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-1-phenylethyl β-D-glucopyranoside 在 phosphate buffer 、 almond-β-glucosidase 作用下， 反应 24.0h， 生成 (S)-(-)-1-苯乙醇
  参考文献：
  名称：

  Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

  摘要：

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.022
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖酰氟 在 三氟化硼乙醚 、 potassium carbonate 、 四甲基胍 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (S)-1-phenylethyl β-D-glucopyranoside
  参考文献：
  名称：

  Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

  摘要：

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.022

文献信息

• Enantioselective Glucosylation of (<i>R</i>,<i>S</i>)-1-Phenylethanol by the Cultured Suspension Cells of Higher Plants
  作者：Ym Sook Lee、Diana I. Ito、Kazuhiko Koya、Shunsuke Izumi、Toshifumi Hirata

  DOI：10.1246/cl.1996.719

  日期：1996.8

  its acetate were transformed into their β-D-glucopyranoside by the cultured suspension cells of Nicotiana tabacum and Catharanthus roseus. The glucosylation with the green N. tabacum cells occurred enantioselectively to give the glucoside of the (S)-alcohol, while the biotransformation with the white N. tabacum cells and C. roseus cells gave preferentially the glucoside of the (R)-alcohol.

  (R,S)-1-苯乙醇及其乙酸盐通过烟草和长春花悬浮培养细胞转化为β-D-吡喃葡萄糖苷。与绿色烟草细胞的糖基化发生对映选择性以产生 (S)-醇的糖苷，而与白色烟草细胞和玫瑰花细胞的生物转化优先产生 (R)-醇的糖苷。
• Diastereoselective Formation of Disaccharides from (<b><i>RS</i></b>)-1-Phenylethanol by Cultured Cells of<b><i>Catharanthus roseus</i></b>
  作者：Toshifumi Hirata、Kei Shimoda、Takeshi Fujino、Shin-ya Yamane、Shinji Ohta

  DOI：10.1246/bcsj.74.539

  日期：2001.3

  The biotransformation of (RS)-1-phenylethanol with cultured cells of Catharanthus roseus gave its vicianoside [α-L-arabinopyranosyl-(1-6)-β-D-glucopyranoside], primeveroside [β-D-xylopyranosyl-(1-6)-β-D-glucopyranoside] and gentiobioside [β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside] via the corresponding glucoside. It was found that primeveroside and gentiobioside were enantioselectively composed of only (R)-1-phenylethanol as its aglycone moiety.

  用培养的长春花细胞对（RS）-1-苯乙醇进行生物转化，可以得到维基苷[α-L-阿拉伯呋喃糖-(1-6)-β-D-葡萄糖呋喃糖苷]、初花苷[β-D-木糖呋喃糖-(1-6)-β-D-葡萄糖呋喃糖苷]和绒毛苷[β-D-葡萄糖呋喃糖-(1-6)-β-D-葡萄糖呋喃糖苷]，通过相应的糖苷转化。研究发现，初花苷和绒毛苷的心变异构体仅由（R）-1-苯乙醇作为其苷元部分组成。
• Enzymatic resolution of (RS)-1-phenylalkyl β-d-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-d-glucosides via plant xylosyltransferase
  作者：Kei Shimoda、Hisashi Katsuragi

  DOI：10.1016/j.tetasy.2010.07.023

  日期：2010.8

  The stereoselective xylosylation of (RS)-1-phenylalkyl beta-D-glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of (RS)-1-phenylethyl beta-D-glucoside afforded (R)-1-phenylethyl beta-primeveroside and (S)-1-phenylethyl beta-D-glucoside. The (R)-selective xylosylation of (RS)-1-phenylbutyl beta-D-glucoside also occurred to give (R)-1-phenylbutyl p-primeveroside and recovered (S)-1-phenylbutyl beta-D-glucoside. (C) 2010 Elsevier Ltd. All rights reserved.
• Ooi, Yasuhiro; Mitsuo, Naoki; Satoh, Toshio, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 12, p. 5547 - 5550
  作者：Ooi, Yasuhiro、Mitsuo, Naoki、Satoh, Toshio

  DOI：——

  日期：——
• Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases
  作者：Kei Shimoda、Naoji Kubota、Hiroki Hamada

  DOI：10.1016/j.tetasy.2004.06.022

  日期：2004.8

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.