Huang Baohua, Desai Ankur, Zong Hong, Tang Shengzhuang, Leroueil Pascale, Baker James R
Michigan Nanotechnology Institute for Medicine and Biological Sciences, University of Michigan, Ann Arbor, Michigan 48109, USA.
Tetrahedron Lett. 2011 Mar 30;52(13):1411-1414. doi: 10.1016/j.tetlet.2010.12.025.
The synthesis of a generation 5 (G5) poly(amidoamine) (PAMAM) dendrimer platform having cyclooctyne ligands that were subsequently be used for a copper-free Huisgen 1,3-dipolar cycloaddition (click reaction) with azido modified methotrexate is described. The G5 PAMAM dendrimer was first partially (70%) acetylated and then coupled with 20 cyclooctyne ligands through amide bonds. The remaining primary amine groups on the dendrimer surface were neutralized by acetylation. The platform was then "clicked" with different numbers (5, 10, and 17) of γ-azido functionalized methotrexate. The copper-free click reactions were stoichiometric with excellent yields.
描述了具有环辛炔配体的第5代（G5）聚（酰胺胺）（PAMAM）树枝状大分子平台的合成，该平台随后用于与叠氮基修饰的甲氨蝶呤进行无铜的惠斯根1,3-偶极环加成反应（点击反应）。首先将G5 PAMAM树枝状大分子部分（70%）乙酰化，然后通过酰胺键与20个环辛炔配体偶联。树枝状大分子表面剩余的伯胺基团通过乙酰化中和。然后将该平台与不同数量（5、10和17）的γ-叠氮基功能化甲氨蝶呤进行“点击”反应。无铜点击反应是化学计量的，产率优异。
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