Vitamin B_12s

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: Vitamin B_12s
• 英文别名: cob(I)alamin；Vitamin B (12s), Hydridocobalamin
• 化学式: C₆₂H₈₉CoN₁₃O₁₄P
• 分子量: 1330.43
• InChiKey: OMAOKVYASDIYQG-DSRCUDDDSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  91.0
• 可旋转键数：
  26.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  451.23
• 氢给体数：
  10.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  Vitamin B_12s 在 sodium selenite 作用下， 生成 Vitamin B_12r
  参考文献：
  名称：

  Interaction between super-reduced cobalamin and selenite

  摘要：

  The kinetics of the reaction between the two-electron reduced form of cobalamin (super-reduced cobalamin, cob(I)alamin, or Cbl(I)) and sodium selenite in an alkaline medium is studied spectrophotometrically. It is shown that the selenite rapidly oxidizes Cbl(I) to cob(II)alamin (Cbl(II)). It is established that the active form of the oxidant is the protonated selenite anion (HSeO3 (-)), which receives six electrons during the reaction and transforms into HSe-. The reactions of cob(I)alamin oxidation by selenite and sulfite are compared.

  DOI：

  10.1134/s003602441711005x
• 作为产物：
  描述：

  Fluormethylphosphito-P-cobalamin 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 0.03h， 生成 Vitamin B_12s
  参考文献：
  名称：

  Bieganowski, Rainer; Friedrich, Wilhelm, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1980, vol. 35, # 11, p. 1335 - 1340

  摘要：

  DOI：

文献信息

• Studies on Vitamin B₁₂ and Related Compounds, 50 Synthesis of Substituted Alkylcobalamins from Vitamin B_12r and Radicals Generated from Aldehydes, Alcohols and Ethers under "Oxidizing-Reducing" Conditions. A New Synthesis of Coenzyme B₁₂ [1]
  作者：Gerhard N. Schrauzer、Masao Hashimoto、Abdussalam Maihub

  DOI：10.1515/znb-1980-0515

  日期：1980.5.1

  Organic radicals generated by the oxidation of aldehydes, alcohols and ethers under reducing conditions are trapped by vitamin B12r to yield substituted organocobalamins. From higher n-alkyl aldehydes, acylcobalamins are formed. With acetaldehyde, a mixture of acetylcobalamin and of methylcobalamin is obtained due to the spontaneous decarbonylation of the CH3CO· radical. From saturated alcohols, w

  醛、醇和醚在还原条件下氧化产生的有机自由基被维生素 B12r 捕获，产生取代的有机钴胺素。由高级正烷基醛形成酰基钴胺素。使用乙醛，由于 CH3CO· 自由基的自发脱羰，得到乙酰钴胺素和甲基钴胺素的混合物。由饱和醇生成正羟基烷基钴胺素，而正构烷氧基烷基钴胺素在与醚生成的自由基的相应反应中形成。如果在有机底物氧化过程中保持还原条件，则可获得最大的有机钴胺素产量。这可以通过使用 V(III) 盐作为还原剂和缓慢加入氧化剂（例如 O2、H2O2、芬顿试剂、或电化学产生的氧化等效物）。与 5'-脱氧腺苷一起形成 5'-脱氧腺苷钴胺素。
• Cob(I)alamin-Catalyzed Skeletal Migrations Observed during the Reduction of 4?-(tert-Butyl)-1?-(1-methylvinyl)cyclohexanecarbaldehyde
  作者：Terence S. Wan、Albert Fischli

  DOI：10.1002/hlca.19840670726

  日期：1984.11.7

  The cob(I) alamin(1(I))-catalyzed2 transformation of the aldehyde 2 has been studied (cf. Table 1). Kinetic examinations showed a rapid isomerization of 2 to 3 (cf. Fig. 1 and 2). From the transformations in glacial AcOH, the two cyclopropanols 5 and 7 were isolated as main products (cf. Tables 1–3 and Fig. 1 and 2). Using large amounts of 1(I), the aldehyde 4 was very slowly transformed. Accepting

  已经研究了由钴（I）丙氨酸（1（I））催化的醛2的2转化（参见表1）。动力学检查显示2至3的快速异构化（参见图1和2）。从冰川AcOH的转化中，分离出两种环丙醇5和7作为主要产物（参见表1-3和图1和2）。使用大量的1（I）醛4非常缓慢地转变。接受的6中间形成连共复合物，即甲，乙，Ç，d，È和˚F （参见方案），所有观察到的可以解释的产物的产生。
• Mechanism of the cyanide-induced formation of methyl acetate from [(methoxycarbonyl)methyl]cobalamin
  作者：William W. Reenstra、Robert H. Abeles、William P. Jencks

  DOI：10.1021/ja00368a017

  日期：1982.2
• Transalkylation of Phosphotriesters Using Cob(I)alamin:  Toward Specific Determination of DNA−Phosphate Adducts
  作者：Johanna Haglund、Adnan Rafiq、Lars Ehrenberg、Bernard T. Golding、Margareta Törnqvist

  DOI：10.1021/tx990135m

  日期：2000.4.1

  The supernucleophilic cobalt compound, cob(I)alamin, has been kinetically characterized with respect to its ability to bring about transalkylation of adducts to DNA phosphates (phosphotriesters). The reactivity of cob(I)alamin toward different phosphotriesters (model compounds and methylated DNA), as well as its specificity toward DNA-phosphate adducts, has been investigated. Through nucleophilic displacement on the alkyl by cob(I)alamin, the alkyl groups (methyl and ethyl) were transferred from phosphotriesters within minutes at room temperature. In contrast, methylated nucleosides (base adducts) were stable in the presence of cob(I)alamin.
• Pillai, G. Chithambarathanu; Bose, Rathindra N.; Gould, Inorganic Chemistry, <hi>1987</hi>, vol. 26, # 19, p. 3120 - 3123
  作者：Pillai, G. Chithambarathanu、Bose, Rathindra N.、Gould

  DOI：——

  日期：——