5′-Vitamin B12 derivatives suitable for bioconjugation via the amide bond†,Organic & Biomolecular Chemistry

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5′-Vitamin B12 derivatives suitable for bioconjugation via the amide bond†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-01-08 00:00:00 , DOI: 10.1039/c7ob02898a
A. Jackowska _{1,

2,

3} , M. Chromiński _{1,

2,

3} , M. Giedyk _{1,

2,

3} , D. Gryko _{1,

2,

3}

Affiliation

Vitamin B₁₂ is an attractive candidate for a drug or an imaging-agent carrier into cells, due to its dietary uptake and well established transport through glycoproteins. Utilization of this system requires an appropriate functionalization of vitamin B₁₂ that both allows for the conjugation of therapeutics and does not interrupt its recognition by transport proteins. Modifications at the 5′-position on the ribose moiety are among a few approaches which meet the criteria. In this article we present vitamin B₁₂ derivatives bearing either the amino or the carboxylic group at the 5′-position. The presence of these functional groups enables conjugation of biologically important molecules to vitamin B₁₂via the amide bond. The established method is not only limited to organic media but also works in an aqueous environment, giving the desired products in very good yields.

中文翻译：

适用于通过酰胺键生物结合的 5'-维生素B ₁₂衍生物†

维生素B ₁₂由于其饮食摄取和通过糖蛋白的良好运输，因此是吸引药物或显像剂载体进入细胞的诱人候选物。利用该系统需要适当地功能化维生素B ₁₂，该功能既可以结合治疗剂，又不会干扰转运蛋白的识别。满足标准的几种方法包括在核糖部分5'-位的修饰。在本文中，我们介绍了在5'位带有氨基或羧基的维生素B ₁₂衍生物。这些官能团的存在使生物学上重要的分子能够通过以下方式与维生素B ₁₂结合：酰胺键。既定的方法不仅限于有机介质，而且还可以在水性环境中使用，从而以非常高的收率获得所需的产品。

更新日期：2018-01-08

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