cob(II)alamin | 13408-78-1

• 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: cob(II)alamin
• 英文别名: cob(I)alamin；cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,4Z,7S,12S,13S,14Z,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-21-id-3-yl]propanoylamino]propan-2-yl] phosphate
• CAS: 13408-78-1
• 化学式: C₆₂H₈₈CoN₁₃O₁₄P
• 分子量: 1329.43
• InChiKey: NSLAUEAQDBERRV-DSRCUDDDSA-L

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  91
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  452
• 氢给体数：
  9
• 氢受体数：
  19

安全信息

• WGK Germany：
  1
• RTECS号：
  GG3750000
• 海关编码：
  2936260000

反应信息

• 作为反应物：
  描述：

  cob(II)alamin 在 聚合甲醛 作用下， 反应 0.08h， 生成 Vitamin B_12r
  参考文献：
  名称：

  Tetrazole derivatives and matrices as novel cobalamin coordinating compounds

  摘要：

  Cobalamin (Cbl, vitamin B-12) consists of two moieties: (i) the corrin ring with the central Co-ion in the oxidation states Co3+/2+/1+ and (ii) the nucleotide side chain. The lower position of the ring is typically occupied by the nucleotide base (Bzm), whereas the upper surface coordinates exchangeable ligands. We have found that amino-tetrazole can coordinate to H2O center dot Cbl (Co3+) with K-d = 10(-5)-10(-6) M. A specific group (presumably tetrazole, TZ) can be easily created in CNBr-activated Sepharose by treatment with N-3(-). The prepared matrix (STZ) contained approximate to 10 mM of the active groups, which bound H2O center dot corrinoids with K-d = 10(-5)-10(-6) M. Stability of STZ-Cbl bonds gradually increased and reached K-d = 10(-7) M over 10-20 h (20 degrees C, pH 6-7). This effect can be ascribed to partial displacement of Bzm and coordination of TZ to the lower position. The binding was most efficient at pH 4-7 and low ionic strength, yet, noticeable adsorption took place even at extreme conditions, pH 1-9 and I = 0-2 M. Reduced corrins (Co2+) also exhibited high affinity for STZ. The bound ligands could be eluted as H2O center dot Cbl (pH 0), HO center dot Cbl (pH 14) or diCN center dot Cbl (pH 9-12, CN-). The adsorbent is applicable for one-step purification of corrins from a crude extract; separation of aquo- and diaquo-forms; specific capturing of H2O center dot Cbl from a mixture containing organo-Cbls or protein-bound Cbl, analysis of peptide-Cbl dissociation kinetics, etc. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.08.081
• 作为产物：
  描述：

  hydroxocobalamin hydrochloride 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 生成 cob(II)alamin
  参考文献：
  名称：

  Vanadium–vitamin B12 bioconjugates as potential therapeutics for treating diabetes

  摘要：

  报告了第一种钒维生素 B12 生物共轭物的合成和降血糖特性。

  DOI：

  10.1039/b806598e

文献信息

• Spectroscopic and Computational Studies of Co¹⁺Cobalamin:  Spectral and Electronic Properties of the “Superreduced” B₁₂ Cofactor
  作者：Mathew D. Liptak、Thomas C. Brunold

  DOI：10.1021/ja061433q

  日期：2006.7.19

  attractive target for the in situ bioremediation of halogenated waste. To gain insight into the geometric, electronic, and vibrational properties of this highly reactive species, electronic absorption, circular dichroism (CD), magnetic CD, and resonance Raman (rR) spectroscopies have been employed in conjunction with density functional theory (DFT), time-dependent DFT, and combined quantum mechanics/molecular

  4 配位低自旋钴胺素 (Co1+Cbl) 物种，可通过甲基钴胺素中 Co-C 键的异裂裂解或维生素 B12 的双电子还原获得，是最常见的一种迄今为止已知的强大亲核试剂。Co1+Cbl 的超亲核性已被许多钴胺素依赖性酶（例如 B12 依赖性蛋氨酸合酶）和参与 B12 生物合成的酶（包括人腺苷转移酶）利用。Co1+Cbl 超亲核试剂的无毒性质也使其成为卤化废物原位生物修复的有吸引力的目标。为了深入了解这种高反应性物质的几何、电子和振动特性、电子吸收、圆二色性 (CD)、磁性 CD、和共振拉曼 (rR) 光谱已与密度泛函理论 (DFT)、瞬态 DFT 和组合量子力学/分子力学计算结合使用。总的来说，我们的结果表明 Co1+Cbl 的超亲核性可归因于基于 Co 3dz2 的 HOMO 的大不稳定及其相对于 corrin 大环的有利取向，这最大限度地减少了亲核攻击期间的空间排斥。CD 光谱中的一个强烈特征和
• Unusual Aerobic Stabilization of Cob(I)alamin by a B₁₂-Trafficking Protein Allows Chemoenzymatic Synthesis of Organocobalamins
  作者：Zhu Li、Nicholas A. Lesniak、Ruma Banerjee

  DOI：10.1021/ja5077316

  日期：2014.11.19

  CblC, a B-12 trafficking protein, exhibits glutathione transferase and reductive decyanase activities for processing alkylcobalamins and cyanocobalamin, respectively, to a common intermediate that is subsequently converted to the biologically active forms of the cofactor. We recently discovered that the Caenorhabditis elegans CblC catalyzes thiol-dependent decyanation of CNCbl and reduction of OH(2)Cbl and stabilizes the paramagnetic cob(II)alamin product under aerobic conditions. In this study, we report the striking ability of the worm CblC to stabilize the highly reactive cob(I)alamin product of the glutathione transferase reaction. The unprecedented stabilization of the supernucleophilic cob(I)alamin species under aerobic conditions by the intrinsic thiol oxidase activity of CblC, was exploited for the chemoenzymatic synthesis of organocobalamin derivatives under mild conditions.
• Vanadium–vitamin B12 bioconjugates as potential therapeutics for treating diabetes
  作者：Riya Mukherjee、Edward G. Donnay、Michal A. Radomski、Catherine Miller、Duane A. Redfern、Arne Gericke、Derek S. Damron、Nicola E. Brasch

  DOI：10.1039/b806598e

  日期：——

  The synthesis and blood glucose lowering properties of the first vanadium–vitamin B12 bioconjugates are reported.

  报告了第一种钒维生素 B12 生物共轭物的合成和降血糖特性。
• Tetrazole derivatives and matrices as novel cobalamin coordinating compounds
  作者：Sergey N. Fedosov、Lars Berglund、Ebba Nexø、Torben E. Petersen

  DOI：10.1016/j.jorganchem.2006.08.081

  日期：2007.2

  Cobalamin (Cbl, vitamin B-12) consists of two moieties: (i) the corrin ring with the central Co-ion in the oxidation states Co3+/2+/1+ and (ii) the nucleotide side chain. The lower position of the ring is typically occupied by the nucleotide base (Bzm), whereas the upper surface coordinates exchangeable ligands. We have found that amino-tetrazole can coordinate to H2O center dot Cbl (Co3+) with K-d = 10(-5)-10(-6) M. A specific group (presumably tetrazole, TZ) can be easily created in CNBr-activated Sepharose by treatment with N-3(-). The prepared matrix (STZ) contained approximate to 10 mM of the active groups, which bound H2O center dot corrinoids with K-d = 10(-5)-10(-6) M. Stability of STZ-Cbl bonds gradually increased and reached K-d = 10(-7) M over 10-20 h (20 degrees C, pH 6-7). This effect can be ascribed to partial displacement of Bzm and coordination of TZ to the lower position. The binding was most efficient at pH 4-7 and low ionic strength, yet, noticeable adsorption took place even at extreme conditions, pH 1-9 and I = 0-2 M. Reduced corrins (Co2+) also exhibited high affinity for STZ. The bound ligands could be eluted as H2O center dot Cbl (pH 0), HO center dot Cbl (pH 14) or diCN center dot Cbl (pH 9-12, CN-). The adsorbent is applicable for one-step purification of corrins from a crude extract; separation of aquo- and diaquo-forms; specific capturing of H2O center dot Cbl from a mixture containing organo-Cbls or protein-bound Cbl, analysis of peptide-Cbl dissociation kinetics, etc. (C) 2006 Elsevier B.V. All rights reserved.