L-山梨糖酮 | 49865-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: L-山梨糖酮
• 英文名称: L-sorbosone
• 英文别名: L-xylo-3,4,5,6-Tetrahydroxy-2-oxo-hexanal；L-xylo-[2]Hexosulose；L-Sorboson；L-Guloson；L-Idoson；(3S,4R,5S)-3,4,5,6-tetrahydroxy-2-oxohexanal
• CAS: 49865-02-3
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: DCNMIDLYWOTSGK-KVQBGUIXSA-N

物化性质

• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-山梨糖酮 在 水 、 溴 作用下， 生成 2-酮-L-古洛糖酸
  参考文献：
  名称：

  Micheel et al., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1934, vol. 225, p. 13,25

  摘要：

  DOI：
• 作为产物：
  描述：

  L-山梨糖 在 甲醇 、 copper diacetate 作用下， 生成 L-山梨糖酮
  参考文献：
  名称：

  Weidenhagen, 1937, vol. 87, p. 711,715

  摘要：

  DOI：

文献信息

• Reactivity of sorbose dehydrogenase from <i>Sinorhizobium</i> sp. 97507 for 1,5-anhydro-<scp>d</scp>-glucitol
  作者：Toshio Araki、Tomoko Nakatsuka、Fuminao Kobayashi、Emi Watanabe-Ishimaru、Hirokazu Sanada、Takashi Tamura、Kenji Inagaki

  DOI：10.1080/09168451.2015.1012148

  日期：2015.7.3

  Purified recombinant sorbose dehydrogenase from Sinorhizobium sp. 97507 exhibited high reactivity for 1,5-anhydro-d-glucitol (1,5-AG) and l-sorbose, but little activity for the other sugars or sugar alcohols tested. Kinetic analysis revealed that its catalytic efficiency (kcat/Km) for l-sorbose and 1,5-AG is 1.8 × 102 and 1.5 × 102 s−1·M−1, respectively.

  从Sinorhizobium sp. 97507纯化的重组山梨糖脱氢酶对1,5-脱氢-D-葡萄糖醇（1,5-AG）和L-山梨糖表现出很高的反应性，但对其他糖或糖醇的活性很小。动力学分析表明，其对L-山梨糖和1,5-AG的催化效率（kcat/Km）分别为1.8 × 102和1.5 × 102 s−1·M−1。
• Enzyme and process for producing the same
  申请人：Hoffmann-La Roche Inc.

  公开号：US04902617A1

  公开（公告）日：1990-02-20

  The present invention relates to novel enzyme having L-sorbosone dehydrogenase activity and a process for producing the same. This L-Sorbosone dehydrogenase enzyme provided by the present invention catalyzes the oxidation of L-sorbosone to 2-keto-L-gulonic acid in the presence of nicotinamide adenine dinucleotide or nicotinamide adenine dinucleotide phosphate as a coenzyme. 2-KGA is an important precursor for the production of vitamin C.

  本发明涉及一种具有L-山梨酮脱氢酶活性的新型酶及其生产方法。本发明提供的L-山梨酮脱氢酶酶催化在存在烟酰胺腺嘌呤二核苷酸或烟酰胺腺嘌呤二核苷酸磷酸形式的辅酶下，将L-山梨酮氧化为2-酮-L-古龙酸。2-KGA是生产维生素C的重要前体。
• Process for producing vitamin c
  申请人：Hoshino Tatsuo

  公开号：US20060121582A1

  公开（公告）日：2006-06-08

  The present invention relates to a process for the production of vitamin C from L sorbosone using an aldehyde dehydrogenase which is isolated from Gluconobacter oxydans DSM 4025 (FERM BP-3812), said enzyme having the following physicochemical properties: (a) molecular weight of 150,000±6,000 Da or 230,000±9,000 Da (consisting of 2 or 3 homologous subunits, each subunit having a molecular weight of 75,000±3,000 Da); (b) substrate specificity as active on aldehyde compounds; (c) Cofactors are pyrroloquinoline quinone and heme c; (d) Optimum pH between 6.4 and 8.2 for vitamin C production from L-sorbosone; and (e) as inhibitors Co 2+ , Cu 2+ , Fe 2+ , Ni 2+ , Zn 2+ , monoiodoacetate and ethylendiamine tetraacetic acid. The process is performed in the presence of a suitable electron acceptor and the vitamin C isolated from the reaction mixture.

  本发明涉及一种利用从Gluconobacter oxydans DSM 4025（FERM BP-3812）中分离出的醛脱氢酶从L-山梨醇酮制备维生素C的方法，该酶具有以下物理化学性质：（a）分子量为150,000±6,000 Da或230,000±9,000 Da（由2或3个同源亚基组成，每个亚基的分子量为75,000±3,000 Da）；（b）底物专一性为活性醛化合物；（c）辅因子为吡咯喹啉醌和血红素c；（d）在pH 6.4和8.2之间为从L-山梨醇酮制备维生素C的最适pH；（e）抑制剂为Co2+、Cu2+、Fe2+、Ni2+、Zn2+、单碘乙酸和乙二胺四乙酸。该过程在适当的电子受体的存在下进行，并从反应混合物中分离维生素C。
• Aldehyde dehydrogenase II
  申请人：Hoshino Tatsuo

  公开号：US20050153412A1

  公开（公告）日：2005-07-14

  The present invention concerns a novel aldehyde dehydrogenase having the following physico-chemical properties: a molecular weight of 100,000±10,000 Da which comprises two homologous subunits or a molecular weight of 150,000±15,000 Da which comprises three homologous subunits, each subunit having a molecular weight of 55,000±2,000 Da; dehydrogenase activity on L-sorbosone, D-Glucosone, D-glucose and D-xylose; utilizes as cofactor pyrroloquinoline quinone; has an optimum pH of from 6.5 to 8.0 for the production of vitamin C and an optimum pH of about 9.0 for the production of 2-keto-L-gulonic acid from L-sorbosone; and is inhibited by Co 2+ , Cu 2+ , Fe 3+ , Ni 2+ , Zn 2+ , and monoiodoacetate, is derived from a microorganism belonging to the genus Gluconobacter.

  本发明涉及一种新型醛脱氢酶，具有以下物理化学性质：分子量为100,000±10,000 Da，包括两个同源亚基或分子量为150,000±15,000 Da，包括三个同源亚基，每个亚基的分子量为55,000±2,000 Da；对L-山梨醇酮、D-葡糖酮、D-葡萄糖和D-木糖具有脱氢酶活性；以吡咯喹啉醌为辅因子；在pH 6.5至8.0的最适条件下生产维生素C，在pH约9.0的最适条件下从L-山梨醇酮生产2-酮-L-古洛酸；并且受到Co2+、Cu2+、Fe3+、Ni2+、Zn2+和单碘乙酸盐的抑制，来源于属于葡萄糖酸杆菌属的微生物。
• Aldehyde dehydrogenase enzyme
  申请人：Roche Vitamins Inc.

  公开号：US05776742A1

  公开（公告）日：1998-07-07

  An aldehyde dehydrogenase having the physico-chemical properties: molecular weight: 91,000.+-.5,000; substrate specificity:active on aldehyde compounds; inhibition: by Cu.sup.2+, Zn.sup.2+, Ni.sup.2 + and ethylenediamine tetraacetic acid; optimum pH: 6.0-8.5; optimum temperature: 20.degree.-40.degree. C.; and stimulator: Ca.sup.2+ and pyrroloquinoline quinone, is derived from a microorganism belonging to the genus Gluconobacter. Said aldehyde dehydrogenase can be produced by cultivating a microorganism of the genus Gluconobacter which is capable of producing an aldehyde dehydrogenase having the above properties, in an aqueous nutrient medium under aerobic conditions, disrupting the cells of the microorganism and isolating and purifying the aldehyde dehydrogenase from the cell-free extract of the disrupted cells of the microorganism. The aldehyde dehydrogenase is useful for the preparation of 2-keto-L-gulonic acid (2-KGA) which can be produced from L-sorbosone by contacting L-sorbosone with (i) the aldehyde dehydrogenase in the presence of an electron acceptor, (ii) a Gluconobacter microorganism capable of producing the aldehyde dehydrogenase in an aqueous medium under aerobic conditions or (iii) a cell-free extract of said microorganism, and in each case isolating the resulting 2-keto-L-gulonic acid from the reaction mixture.

  一种醛脱氢酶具有以下物理化学特性：分子量：91,000.+-.5,000；底物特异性：对醛类化合物具有活性；抑制：被Cu.sup.2+、Zn.sup.2+、Ni.sup.2+和乙二胺四乙酸抑制；最适pH：6.0-8.5；最适温度：20℃-40℃；刺激剂：Ca.sup.2+和吡咯喹啉醌，来源于属于葡萄糖酸杆菌属的微生物。可以通过在水性营养培养基中培养能够产生具有上述特性的醛脱氢酶的葡萄糖酸杆菌属微生物，破坏微生物的细胞并从破碎的细胞的无细胞提取物中分离和纯化醛脱氢酶来制备该醛脱氢酶。该醛脱氢酶用于制备2-酮-L-古龙酸（2-KGA），可以通过将L-索伯酮与（i）电子受体存在下的醛脱氢酶，（ii）在水性培养基中能够产生该醛脱氢酶的葡萄糖酸杆菌微生物或（iii）该微生物的无细胞提取物接触，然后从反应混合物中分离所得的2-酮-L-古龙酸来制备。