cyanocobalamin

• 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: cyanocobalamin
• 英文别名: vitamin B₁₂
• 化学式: CCoN*C₆₂H₈₈N₁₃O₁₄P
• 分子量: 1355.44
• InChiKey: RMRCNWBMXRMIRW-WZHZPDAFSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  cyanocobalamin 、 bis(1,2,4-triazol-4-yl)methanone 生成
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Structural Determination of 5‘-OH α-Ribofuranoside Modified Cobalamins via ¹³C and DEPT NMR
  作者：Robert A. Horton、Joshua D. Bagnato、Charles B. Grissom

  DOI：10.1021/jo0340399

  日期：2003.9.1

  A protocol for the rapid NMR characterization of cobalamin (vitamin B(12)) analogues with 5'-hydroxy-alpha-ribofuranoside modification is reported. The structure of cyanocobalamin in DMSO-d(6) has been assigned using COSY, NOESY, HSQC, and HMBC NMR methods. The robust precision of (13)C NMR assignments in DMSO-d(6) allows for the rapid structural determination of 5'-hydroxy-alpha-ribofuranosyl cyanocobalamin

  报道了具有5'-羟基-α-核糖呋喃糖苷修饰的钴胺素（维生素B（12））类似物的快速NMR表征协议。已使用COSY，NOESY，HSQC和HMBC NMR方法指定了DMSO-d（6）中氰钴胺的结构。DMSO-d（6）中（13）C NMR分配的稳健精度允许快速结构测定仅具有1-D（13）C和DEPT NMR光谱的5'-羟基-α-核呋喃糖基氰基考拉明衍生物毫克衍生的钴胺素。使用此方法，确定了四种钴胺素类似物的（13）C NMR共振，其中在α-核呋喃糖苷环中发生的（13）C化学位移的变化最大。在DMSO-d（6）中，可以提高钴胺素的浓度大于30 mM，以提高信噪比。
• Synthesis and Structure of Vitamin B12-Derivatives with a Modified Ribose-Unit
  作者：Renate B. Hannak、Sigrid Gschösser、Klaus Wurst、Bernhard Kräutler

  DOI：10.1007/s00706-007-0752-9

  日期：2007.9

  The acylation at the 5′-OH group of the ribose-unit of vitamin B12 (cyanocobalamin) or of aquocobalamin with two conventional reagents gave mono-acylated B12-derivatives with good to very high selectivity. The site of the modification was deduced from spectral data of the products and was further supported by the crystal structure data of three such modified B12-derivatives. These three B12-derivatives

  用两种常规试剂在维生素B 12（氰基钴胺）或水钴胺的核糖单元的5'-OH基团上进行酰化，得到具有良好或非常高的选择性的单酰化的B 12-衍生物。从产物的光谱数据推断出修饰的位点，并进一步得到三种这样的修饰的B 12衍生物的晶体结构数据的支持。发现这三种B 12衍生物在空间群 P 2 1 2 1 2 1中结晶。 ，无论附件的性质如何。在2'-OH或在B 12-分子中的其他地方官能化的情况下，在5'-OH上的酰化作用已用于保护（或封闭）该基团。双功能琥珀酰单元的连接允许制备维生素B 12的进一步修饰的衍生物，并使B 12衍生物与生物载体和其他大分子结合。在水溶液中，结果证明5'-酰基硫醇溶蛋白对酰基官能度的水解损失相当敏感。
• Partial Synthesis of CoαCoβ-Dicyano-176-Norcobinamide
  作者：Philip A. Butler、Shahzad Murtaza、Bernhard Kräutler

  DOI：10.1007/s00706-006-0556-3

  日期：2006.12

  B12-derivatives, homologues of complete vitamin B12-derivatives, lacking the methyl group at carbon 176, stems from the identification of the corrinoid cofactor of the tetrachloroethene reductive dehalogenase of Sulfurospirillum multivorans as 176-nor-pseudovitamin B12. Here we report the partial synthesis of the corrinoid CoαCoβ-dicyano-176-norcobinamide by condensation of cobyric acid and 2-aminoethanol. In addition

  在norvitamin乙最近兴趣12 -衍生物，完整的维生素B的同源物12 -衍生物，缺乏甲基碳在176，从的四氯乙烯还原脱卤酶的类咕啉辅因子的识别茎 Sulfurospirillum multivorans 为176去甲pseudovitamin乙12。此处我们报告的类咕啉钴的部分合成α钴β由cobyric酸和2-氨基乙醇的缩合-dicyano-176-norcobinamide。此外，结晶Co的部分合成α -aquo钴β通过酸-cyanocobyric酸催化维生素B的水解12详细介绍了 Bernhauer等人 先前提出的改进方法和分离程序 。Co的溶液结构α联合β -dicyano-176-norcobinamide研究了光谱和用所述同源物的Co相比α钴β -dicyanocobinamide。标题化合物，钴α联合β -dicyano-176-norcobinamide，表示二氰基形式
• Synthesis and Characterization of a Cobalamin−Colchicine Conjugate as a Novel Tumor-Targeted Cytotoxin
  作者：Joshua D. Bagnato、Alanna L. Eilers、Robert A. Horton、Charles B. Grissom

  DOI：10.1021/jo049953w

  日期：2004.12.1

  Colchicine was derivatized at C7 with p-alkoxyacetophenone and conjugated to cobalamin (vitamin B-12) through an acid-labile hydrazone linker. The cobalamin moiety leads to preferential uptake of the cobalamin-colchicine prodrug by cancer cells, whereupon the hydrazone linker undergoes hydrolysis in the lysosome to unmask colchicine, which acts as a potent cytotoxin by stabilizing microtubules and causing cell death. The bioconjugate is stable in cell culture media and at neutral pH but undergoes hydrolysis with a half-life of 138 min at pH 4.5. The colchicine-cobalamin bioconjugate exhibits nanomolar LC50 values against breast, brain, and melanoma cancer cell lines in culture. Attachment of colchicine to cobalamin is expected to increase the therapeutic index of the drug by limiting the side effects caused by the current nonselective administration of tubulin-targeted chemotherapeutic drugs.
• Intrinsic factor-mediated modulation of cyanocobalamin–N-sulfonyl-acridinium-9-carboxamide chemiluminescence
  作者：Maciej Adamczyk、Donald D Johnson、Phillip G Mattingly、Jeffrey A Moore、You Pan

  DOI：10.1016/j.bmcl.2004.05.062

  日期：2004.8

  Two cyanocobalamin-N-sulfonyl-acridinium-9-carboxamides with linkage through the N-10 or 9-position were prepared from B-12-e-carboxylic acid. The noncovalent association of intrinsic factor with these ligands resulted in specific modulation of the associated chemiluminescence signal either by quenching or changing the emission profile. Either effect was sufficient to formulate a homogeneous assay to detect vitamin B-12 in buffer. (C) 2004 Elsevier Ltd. All rights reserved.