1-O-[β-D-xylopyranosyl-(1-6)-β-D-glucopyranosyl]-(R)-1-phenylethanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-[β-D-xylopyranosyl-(1-6)-β-D-glucopyranosyl]-(R)-1-phenylethanol
• 英文别名: primeveroside；(R)-1-phenylethyl β-primeveroside；(2R,3R,4S,5S,6R)-2-[(1R)-1-phenylethoxy]-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• 化学式: C₁₉H₂₈O₁₀
• 分子量: 416.425
• InChiKey: VXOJXCBBJWLAPR-QNUDGYJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  29
• 可旋转键数：
  6
• 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

• 作为产物：
  描述：

  [5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲基[羟基-(3,4,5-三羟基四氢吡喃-2-基)氧基磷酰]磷酸氢酯 、 (RS)-1-phenylethyl β-D-glucopyranoside 在 plant xylosyltransferase from Catharanthus roseus 作用下， 反应 52.0h， 以30%的产率得到1-O-[β-D-xylopyranosyl-(1-6)-β-D-glucopyranosyl]-(R)-1-phenylethanol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.07.023

文献信息

• 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.