(R)-3,4-dihydroxymandelonitrile | 190383-25-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-3,4-dihydroxymandelonitrile
• 英文别名: (2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyacetonitrile
• CAS: 190383-25-6
• 化学式: C₈H₇NO₃
• 分子量: 165.148
• InChiKey: CRISWXPNFWRXSH-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.48
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  氢氰酸 、 3,4-二羟基苯甲醛 在 (R)-hydroxynitrile lyase from Prunus amygdalus turcomanica Lincz immobilized onto Eupergit CM 作用下， 以 甲基叔丁基醚 、 二甲基亚砜 为溶剂， 反应 72.0h， 以100%的产率得到(R)-3,4-dihydroxymandelonitrile
  参考文献：
  名称：

  Purification, immobilization and characterization of (R)-hydroxynitrile lyase from Prunus amygdalus turcomanica seeds and their applicability for synthesis of enantiopure cyanohydrins

  摘要：

  A hydroxynitrile lyase (HNL) was purified from wild almond seeds (Prunus amygdalus turcomanica Lincz.) for the first time. Native and subunit molecular masses of the HNL were determined as 100 and 25 kDa, respectively indicating that the enzyme is a homotetramer. The purified enzyme was immobilized onto Eupergit CM and Eupergit C 250 L supports and their lyase and carboligation (synthetic) activities were characterized in terms of optimal pH, temperature and kinetic parameters. While the optimal pH of the free HNL for the lyase activity was 6.0, it was 5.5 for both of the immobilized HNLs. Optimal temperature was determined as 25 degrees C for all HNL preparations. For mandelonitrile cleavage, the apparent K-m - V-max values were 0.38 mM - 197.0 U mg protein-1 for the free HNL, 1.30mM - 26.011mg protein(-1) for HNL immobilized onto Eupergit CM (HNL-Eup CM) and 0.95 mM - 17.5 U mg protein(-1) for HNL immobilized onto Eupergit C 250 L (HNL-Eup C 250 L), respectively. For the carboligation activity, the optimal pH was measured as 4.0 and optimal temperature was determined as 5 C for all of the HNL preparations. For mandelonitrile synthesis, the apparent K-m - V-max values were 14.0 mM -2.70 U mg protein(-1) for the free HNL, 41.0 mM - 0.49 U mg protein-1 for HNL-Eup CM and 38.0 mM - 0.54U mg protein(-1) for HNL-Eup C 250 L, respectively. All of the HNL preparations were employed for the synthesis of mandelonitrile, 2-chloromandelonitrile, 3,4-dihydroxymandelonitrile and 2-hydroxy-4-phenyl butyronitrile in a biphasic tert-butyl methyl ether-citrate buffer (pH 4.0) medium. The results showed that the iminobilized HNL preparations were better than the free HNL in the synthesis of abovementioned cyanohydrins except 2-chloromandelonitrile with higher yields and enantiopurities. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.12.019

文献信息

• Process for preparing optically active cyanohydrins and secondary products
  申请人：Clariant GmbH

  公开号：US20020052523A1

  公开（公告）日：2002-05-02

  The present invention relates to a process for preparing optically active cyanohydrins of the formula (II), 1 by reacting an aldehyde of the formula (I) 2 with HCN in a water-immiscible organic solvent in the presence of water, in the absence or presence of a buffer, in the presence of a (R)-hydroxynitrile lyase, where X, Y and Z in formula (II) have the same meaning as in formula (I), independently of each other are identical or different and are H, F, Cl, Br, I, OH, O(C 1 -C 4 -alkyl), OCOCH 3 , NHCOCH 3 , NO 2 or C 1 -C 4 -alkyl.

  本发明涉及一种制备光学活性氰醇的方法，该氰醇的化学式为（II），通过在水不相溶的有机溶剂中，在水的存在下，在缓冲剂的存在或缺失下，以及（R）-羟基腈酶的存在下，将化学式为（I）的醛与HCN反应，其中化学式（II）中的X、Y和Z与化学式（I）中的含义相同，独立于彼此相同或不同，并且为H、F、Cl、Br、I、OH、O（C1-C4-烷基）、OCOCH3、NHCOCH3、NO2或C1-C4-烷基。
• Process for preparing an enzyme extract
  申请人：Clariant GmbH

  公开号：US20020052039A1

  公开（公告）日：2002-05-02

  The present invention relates to a process for preparing an (R)-hydroxynitrile lyase extract by extracting an (R)-hydroxynitrile lyase-containing natural product with water in the absence or presence of a buffer at a pH of 3.3 to 5.5.

  本发明涉及一种制备(R)-羟腈裂解酶提取物的工艺，其方法是在 pH 值为 3.3 至 5.5 的缓冲液不存在或存在的情况下，用水提取含(R)-羟腈裂解酶的天然产物。
• US6653498B2
  申请人：——

  公开号：US6653498B2

  公开（公告）日：2003-11-25