13-O-β-Maltotriosyl-19-O-β-D-glucosyl-steviol | 93973-88-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 13-O-β-Maltotriosyl-19-O-β-D-glucosyl-steviol
• 英文别名: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 93973-88-7；120707-35-9
• 化学式: C₄₄H₇₀O₂₃
• 分子量: 967.026
• InChiKey: RVDLGYWOACCHHM-ZNCUMVHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  67
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  374
• 氢给体数：
  14
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  13-O-β-Maltotriosyl-19-O-β-D-glucosyl-steviol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 13-O-β-Maltotriosyl-steviol
  参考文献：
  名称：

  Darise, Muchsin; Mizutani, Kenji; Kasai, Ryoji, Agricultural and Biological Chemistry, 1984, vol. 48, # 10, p. 2483 - 2488

  摘要：

  DOI：
• 作为产物：
  描述：

  [(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] (1R,4S,5R,9S,10R,13S)-5,9-dimethyl-14-methylidene-13-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate 生成 13-O-β-Maltosyl-19-O-β-D-glucosyl-steviol 、 13-O-β-Maltotriosyl-19-O-β-D-glucosyl-steviol 、 13-O-β-maltotetrosyl-19-β-D-glucosylsteviol 、 13-O-β-maltopentosyl-19-O-β-D-glucosylsteviol
  参考文献：
  名称：

  Further study on the 1,4-.ALPHA.-transglucosylation of rubusoside, a sweet steviol-bisglucoside from Rubus suavissimus.

  摘要：

  悬钩子苷（13-O-β-D-葡萄糖基甜菊醇的 β-D-葡萄糖酯）是 Rubus suavissimus S. Lee 叶子的主要甜味成分，通过 1, 4-α-转葡萄糖基化环糊精葡聚糖转移酶-淀粉系统（CGTase 系统）。将三-和四-葡萄糖基化产物与已经分离的单-和二-葡萄糖基化产物一起分离。对于在 13-O-葡萄糖基部分进行二糖基化和三糖基化的化合物，观察到甜味强度显着增加。这一结果进一步证实了先前报道的甜菊糖苷的1, 4-α-葡萄糖基化化合物的结构-甜度关系。为了保护 19-COO-葡萄糖基部分免受 CGTase 系统的糖基化，19-COO-葡萄糖基部分的 4-羟基被 β-半乳糖苷酶-乳糖系统进行 β-半乳糖基化。这种半乳糖基化化合物通过 CGTase 系统对 13-O-葡萄糖基部分进行区域选择性糖基化，然后酶消除半乳糖基，以提供刚才提到的改进甜味剂的独家制剂。

  DOI：

  10.1271/bbb1961.55.449

文献信息

• Further study on the 1,4-.ALPHA.-transglucosylation of rubusoside, a sweet steviol-bisglucoside from Rubus suavissimus.
  作者：Kazuhiro OHTANI、Yoko AIKAWA、Hiroshi ISHIKAWA、Ryoji KASAI、Sumio KITAHATA、Kenji MIZUTANI、Shigeki DOI、Masaharu NAKAURA、Osamu TANAKA

  DOI：10.1271/bbb1961.55.449

  日期：——

  Rubusoside (the β-D-glucosyl ester of 13-O-β-D-glucosyl-steviol), which is the major sweet principle of leaves of Rubus suavissimus S. Lee, was subjected to 1, 4-α-transglucosylation by the cyclodextringlucanotransferase-starch system (the CGTase system). The tri- and tetra-glucosylated products were isolated together with the mono- and di-glucosylated products, which had already been isolated. A prominent increase in intensity of the sweetness was observed for the compounds which were di- and tri-glucosylated at the 13-O-glucosyl moiety. This result further substantiated the structure-sweetness relationship for 1, 4-α-glucosylated compounds of steviol-glycosides reported previously. For protection of the 19-COO-glucosyl moiety against glucosylation by the CGTase system, the 4-hydroxyl group of the 19-COO-glucosyl moiety was β-galactosylated by the β-galactosidase-lactose system. This galactosylated compound was subjected to a regio-selective glucosylation of the 13-O-glucosyl moiety by the CGTase system, which was followed by enzymic elimination of the galactosyl group to furnish an exclusive preparation of the improved sweeteners just mentioned.

  悬钩子苷（13-O-β-D-葡萄糖基甜菊醇的 β-D-葡萄糖酯）是 Rubus suavissimus S. Lee 叶子的主要甜味成分，通过 1, 4-α-转葡萄糖基化环糊精葡聚糖转移酶-淀粉系统（CGTase 系统）。将三-和四-葡萄糖基化产物与已经分离的单-和二-葡萄糖基化产物一起分离。对于在 13-O-葡萄糖基部分进行二糖基化和三糖基化的化合物，观察到甜味强度显着增加。这一结果进一步证实了先前报道的甜菊糖苷的1, 4-α-葡萄糖基化化合物的结构-甜度关系。为了保护 19-COO-葡萄糖基部分免受 CGTase 系统的糖基化，19-COO-葡萄糖基部分的 4-羟基被 β-半乳糖苷酶-乳糖系统进行 β-半乳糖基化。这种半乳糖基化化合物通过 CGTase 系统对 13-O-葡萄糖基部分进行区域选择性糖基化，然后酶消除半乳糖基，以提供刚才提到的改进甜味剂的独家制剂。
• Darise, Muchsin; Mizutani, Kenji; Kasai, Ryoji, Agricultural and Biological Chemistry, 1984, vol. 48, # 10, p. 2483 - 2488
  作者：Darise, Muchsin、Mizutani, Kenji、Kasai, Ryoji、Tanaka, Osamu、Kitahata, Sumio、et al.

  DOI：——

  日期：——