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首页> 外文期刊>Chemistry: A European journal >6-Azido-6-deoxy-L-idose as a Hetero-Bifunctional Spacer for the Synthesis of Azido-Containing Chemical Probes
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6-Azido-6-deoxy-L-idose as a Hetero-Bifunctional Spacer for the Synthesis of Azido-Containing Chemical Probes

机译：6-Azido-6-脱氧-L-乳糖作为杂双功能间隔基，用于合成含叠氮基的化学探针

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摘要

The design of 6-azido-6-deoxy-L-idose for use as a hetero-bifunctional spacer is reported. The hemiacetal at one terminus is an equivalent of an aldehyde and can react with nucleophiles, such as amino groups and electron-rich aromatics. The azido group at the other terminus bio-orthogonally undergoes a Huisgen [3+2] cycloaddition with an acetylene. The idose derivative exhibited a higher level of reactivity towards oxime formation than a corresponding glucose derivative. The C-13 NMR spectrum of the uniformly C-13-labeled 6-azido-idose indicated that the acyclic forms of the sugar totaled 0.3% of all the isomers, whereas those of glucose totaled 0.01 %. The larger population of the acyclic forms of the idose derivative would result in higher reactivity towards electrophilic addition in comparison with glucose derivatives. Finally, we prepared a C-idosyl epigallocatechin gallate (EGCG) that bears an azido group through C-glycosylation of EGCG with 6-azido-idose. This glycosyl form of the C-idosyl EGCG exhibited a cytotoxicity against U266 cells that was comparable to that of EGCG. These results suggested that the EGCG derivative could be used as an effective chemical probe for the elucidation of EGCG biological functions.
机译：报道了用作杂双功能间隔基的6-叠氮基6-脱氧-L-乳糖的设计。一个末端的半缩醛相当于醛，可以与亲核试剂（例如氨基和富含电子的芳族化合物）反应。生物正交的另一个末端的叠氮基与乙炔进行Huisgen [3 + 2]环加成反应。与相应的葡萄糖衍生物相比，所述的偶氮糖衍生物对肟的反应性更高。均一的C-13标记的6-叠氮基-同糖的C-13 NMR光谱表明，糖的无环形式占所有异构体的0.3％，而葡萄糖的无环形式占0.01％。与葡萄糖衍生物相比，较大数量的无环形式的乳糖合成衍生物将导致对亲电子加成的更高反应性。最后，我们通过用6-叠氮基-ID糖对EGCG进行C-糖基化制备了带有叠氮基的C-亚烷基表没食子儿茶素没食子酸酯（EGCG）。 C-亚烷基EGCG的这种糖基形式对U266细胞具有与EGCG相当的细胞毒性。这些结果表明，EGCG衍生物可以用作阐明EGCG生物学功能的有效化学探针。

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