(1R,2S,3R,5S,6R)-8-氮杂双环[3.2.1]辛烷-1,2,3,6-四醇 | 127414-86-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 中文名称: (1R,2S,3R,5S,6R)-8-氮杂双环[3.2.1]辛烷-1,2,3,6-四醇
• 中文别名: {[4-(2,3-二氢-1,4-苯并二噁英-6-基)-1,3-噻唑-2-基]氨基}(羰基)乙酸-2-氨基乙醇(1:1)
• 英文名称: calystegine B₁
• 英文别名: calystegine B₁；calystegin B₁；calystegine B1；calystegin B1；(1R,2S,3R,5S,6R)-8-Azabicyclo[3.2.1]octane-1,2,3,6-tetrol
• CAS: 127414-86-2
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: BQFFLYRIKODYEN-CXNFULCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  麦芽糖 、 (1R,2S,3R,5S,6R)-8-氮杂双环[3.2.1]辛烷-1,2,3,6-四醇 在 acetate buffer 、 rice α-glucosidase 作用下， 以 水 为溶剂， 反应 9.0h， 以11.3%的产率得到(1R,2S,3R,5S,6R)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8-azabicyclo[3.2.1]octane-1,2,6-triol
  参考文献：
  名称：

  Enzymatic synthesis of the glycosides of calystegines B1 and B2 and their glycosidase inhibitory activities

  摘要：

  Several glycosides of calystegines B-1 and B-2 were synthesized by use of rice a-glucosidase and the whole cells of Rhodotorula lactosa, and their glycosidase inhibitory activities were investigated. Incubation of a mixture of calystegine B-1 and maltose with rice cr-glucosidase gave 3-O-alpha-D-glucopyranosylcalystegine B-1 (2, 11.3%). An enzymatic beta-transglucosylation reaction of calystegines B-1 or B-2 with cellobiose using the whole cells of R. lactosa gave 3-O-beta-D-glucopyranosylcalystegine B-1 (1) (0.9%) or 4-O-beta-D-glucopyranosylcalystegine B-2 (3, 11.2%), respectively, while a similar beta-transgalactosylation of calystegine B-2 from lactose gave 4-O-beta-D-galactopyranosylcalystegine B-2 (4, 10.1%). The glycosylation of calystegines B-1 and B-2 markedly decreased or abolished their inhibition against beta-glucosidase, alpha- or beta-galactosidase. Compound 4 however retained more or less the potency of calystegine B-2 against trehalase. Interestingly, compound 1 was a noncompetitive inhibitor of rice alpha-glucosidase, with a K-1 value of 0.9 +/- 0.1 mu M. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)00227-9

文献信息

• Enzymatic synthesis of the glycosides of calystegines B1 and B2 and their glycosidase inhibitory activities
  作者：Naoki Asano、Atsushi Kato、Haruhisa Kizu、Katsuhiko Matsui、Rhodri C. Griffiths、M.George Jones、Alison A. Watson、Robert J. Nash

  DOI：10.1016/s0008-6215(97)00227-9

  日期：1997.11

  Several glycosides of calystegines B-1 and B-2 were synthesized by use of rice a-glucosidase and the whole cells of Rhodotorula lactosa, and their glycosidase inhibitory activities were investigated. Incubation of a mixture of calystegine B-1 and maltose with rice cr-glucosidase gave 3-O-alpha-D-glucopyranosylcalystegine B-1 (2, 11.3%). An enzymatic beta-transglucosylation reaction of calystegines B-1 or B-2 with cellobiose using the whole cells of R. lactosa gave 3-O-beta-D-glucopyranosylcalystegine B-1 (1) (0.9%) or 4-O-beta-D-glucopyranosylcalystegine B-2 (3, 11.2%), respectively, while a similar beta-transgalactosylation of calystegine B-2 from lactose gave 4-O-beta-D-galactopyranosylcalystegine B-2 (4, 10.1%). The glycosylation of calystegines B-1 and B-2 markedly decreased or abolished their inhibition against beta-glucosidase, alpha- or beta-galactosidase. Compound 4 however retained more or less the potency of calystegine B-2 against trehalase. Interestingly, compound 1 was a noncompetitive inhibitor of rice alpha-glucosidase, with a K-1 value of 0.9 +/- 0.1 mu M. (C) 1997 Elsevier Science Ltd. All rights reserved.