(1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid | 97813-85-9

• 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: (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 97813-85-9；144939-49-1
• 化学式: C₃₈H₆₀O₁₈
• 分子量: 804.884
• InChiKey: UEONVHFOCOWFMZ-GPSAEJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  295
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  13-O-<β-nigerosyl(1->2)-β-D-glucosyl>-19-O-β-D-glucosyl-steviol 在 氢氧化钾 作用下， 反应 1.0h， 以14 mg的产率得到(1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
  参考文献：
  名称：

  Enzymic Production of Sweet Stevioside Derivatives: Transglucosylation by Glucosidases.

  摘要：

  为了提高甜味，并进一步研究甜菊醇苷的结构与甜味之间的关系，研究人员采用多种商用葡糖苷酶对甜菊糖苷进行了转糖基化。结果表明，两种 α-葡萄糖苷酶可产生葡萄糖基化产物。通过普鲁兰酶和普鲁兰对甜菊糖苷进行转葡糖基化，只能得到三种产物：13-O-[β-麦芽三糖基（1→2）-β-葡糖基]-19-O-β-D-葡糖基-烷二醇（1）、13-O-β-maltosyl-(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (2) 和 13-O-β-sophorosyl-19-O-β-maltotriosyl-steviol (3)。所有这些产品都是通过环糊精葡萄糖转移酶淀粉系统对甜菊糖苷进行反式-α-1，4-葡萄糖基化得到的，其中 1 和 2 已被证明是美味而有效的甜味剂。通过生物酶 L 和麦芽糖对甜菊糖苷进行转葡萄糖基化，得到了三种新产品 4、5 和 6，这些化合物的结构被阐明为 13-O-β-sophorosyl-19-O-β-isomaltosyl-steviol(4)、13-O-β-isomaltosyl(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (5) and 13-O-β-nigerosyl(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (6).4 的口感质量明显较高。

  DOI：

  10.1271/bbb1961.55.2959

文献信息

• Enzymic Production of Sweet Stevioside Derivatives: Transglucosylation by Glucosidases.
  作者：Sergei Victrovich LOBOV、Ryoji KASAI、Kazuhiro OHTANI、Osamu TANAKA、Kazuo YAMASAKI

  DOI：10.1271/bbb1961.55.2959

  日期：——

  For the purpose of improving sweetness and a further study on the structure-sweetness relationship of steviol glycosides, transglycosylation of stevioside by a variety of commercial glucosidases was investigated. It was revealed that two α-glucosidases gave glucosylated products. Transglucosylation of stevioside by Pullulanase and pullulan exclusively afforded three products, 13-O-[β-maltotriosyl(1→2)-β-glucosyl]-19-O-β-D-glucosyl-steviol (1), 13-O-β-maltosyl-(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (2) and 13-O-β-sophorosyl-19-O-β-maltotriosyl-steviol (3). All of these products have already been obtained by trans-α-1, 4-glucosylation of stevioside by the cyclodextrin glucano-transferase starch system, and 1 and 2 have been proven to be tasty and potent sweeteners. Transglucosylation of stevioside by Biozyme L and maltose afforded three new products, 4, 5 and 6, the structures of these compounds being elucidated as 13-O-β-sophorosyl-19-O-β-isomaltosyl-steviol(4), 13-O-β-isomaltosyl(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (5) and 13-O-β-nigerosyl(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (6). A significantly high quality of taste was evaluated for 4.

  为了提高甜味，并进一步研究甜菊醇苷的结构与甜味之间的关系，研究人员采用多种商用葡糖苷酶对甜菊糖苷进行了转糖基化。结果表明，两种 α-葡萄糖苷酶可产生葡萄糖基化产物。通过普鲁兰酶和普鲁兰对甜菊糖苷进行转葡糖基化，只能得到三种产物：13-O-[β-麦芽三糖基（1→2）-β-葡糖基]-19-O-β-D-葡糖基-烷二醇（1）、13-O-β-maltosyl-(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (2) 和 13-O-β-sophorosyl-19-O-β-maltotriosyl-steviol (3)。所有这些产品都是通过环糊精葡萄糖转移酶淀粉系统对甜菊糖苷进行反式-α-1，4-葡萄糖基化得到的，其中 1 和 2 已被证明是美味而有效的甜味剂。通过生物酶 L 和麦芽糖对甜菊糖苷进行转葡萄糖基化，得到了三种新产品 4、5 和 6，这些化合物的结构被阐明为 13-O-β-sophorosyl-19-O-β-isomaltosyl-steviol(4)、13-O-β-isomaltosyl(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (5) and 13-O-β-nigerosyl(1→2)-β-D-glucosyl]-19-O-β-D-glucosyl-steviol (6).4 的口感质量明显较高。