Development of a multifunctional neoglycoside auxiliary for applications in glycomics research.
Development of a multifunctional neoglycoside auxiliary for applications in glycomics research.
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DOI：
10.1039/d1ob00941a
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发表时间：
2021-07
影响因子：
3.2
通讯作者：
Thamrongsak Cheewawisuttichai;Matthew Brichacek
中科院分区：
文献类型：
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作者：
Thamrongsak Cheewawisuttichai;Matthew Brichacek
经三步反应合成了一种新型多功能含四嗪的新糖苷类助剂，总收率28%。在水性条件下（pH = 4.7），用DMF作为共溶剂，将羟胺与未保护的碳水化合物缀合，以提供产率在51%和68%之间的新糖苷。这种辅助剂在分离和纯化复杂的碳水化合物混合物、糖基转移酶延伸过程中的相容性以及与化学探针的直接缀合方面显示出广泛的优势。此外，在酸性条件下（0.25%TFA的H2O溶液）可以96%的产率除去助剂，保留完整的糖苷键。因此，含四嗪的新糖苷类助剂可用于促进未来的糖组学研究。
A novel, multifunctional, tetrazine-containing neoglycoside auxiliary has been synthesized in three steps and 28% overall yield. The oxyamine was conjugated with unprotected carbohydrates under aqueous conditions (pH = 4.7), with DMF as a cosolvent, to provide neoglycosides in yields ranging between 51% and 68%. This auxiliary displayed broad advantages in the isolation and purification of complex carbohydrate mixtures, compatibility during extension by glycosyltransferases, and direct conjugation to chemical probes. Furthermore, the auxiliary can be removed in 96% yield under acidic conditions (0.25% TFA in H2O) that leave glycosidic linkages intact. Thereby, the tetrazine-containing neoglycoside auxiliary can serve to facilitate future glycomics investigations.