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Synthesis and Characterization of Versatile O-Glycan Precursors for Cellular O-Glycomics.
ACS Synthetic Biology ( IF 4.7 ) Pub Date : 2019-10-31 , DOI: 10.1021/acssynbio.9b00168 Qing Zhang 1 , Zhonghua Li 2 , Tatiana Chernova 2 , Varma Saikam 1 , Richard Cummings 3 , Xuezheng Song 2 , Tongzhong Ju 4 , David F Smith 2 , Peng G Wang 1
ACS Synthetic Biology ( IF 4.7 ) Pub Date : 2019-10-31 , DOI: 10.1021/acssynbio.9b00168 Qing Zhang 1 , Zhonghua Li 2 , Tatiana Chernova 2 , Varma Saikam 1 , Richard Cummings 3 , Xuezheng Song 2 , Tongzhong Ju 4 , David F Smith 2 , Peng G Wang 1
Affiliation
Protein O-glycosylation is a universal post-translational modification and plays essential roles in many biological processes. Recently we reported a technology termed cellular O-glycome reporter/amplification (CORA) to amplify and profile mucin-type O-glycans of living cells growing in the presence of peracetylated Benzyl-α-GalNAc (Ac3GalNAc-α-Bn). However, the application and development of the CORA method are limited by the properties of the precursor benzyl aglycone, which is relatively inert to further chemical modifications. Here we described a rapid parallel microwave-assisted synthesis of Ac3GalNAc-α-Bn derivatives to identify versatile precursors for cellular O-glycomics. In total, 26 derivatives, including fluorescent and bioorthogonal reactive ones, were successfully synthesized. The precursors were evaluated for their activity as acceptors for T-synthase and for their ability to function as CORA precursors. Several of the precursors possessing useful functional groups were more efficient than Ac3GalNAc-α-Bn as T-synthase acceptors and cellular O-glycome reporters. These precursors will advance the CORA technology for studies of functional O-glycomics.
中文翻译:
用于细胞O-糖蛋白的多功能O-糖基前体的合成与表征。
蛋白质O-糖基化是一种普遍的翻译后修饰,在许多生物学过程中都起着至关重要的作用。最近,我们报道了技术称为蜂窝O型糖组记者/扩增(CORA)扩增和轮廓在全乙酰苄基α-的GalNAc(AC的存在下生长的活细胞粘蛋白型O-聚糖3的GalNAc-α-BN)。然而,CORA方法的应用和发展受到前体苄基糖苷配基的性质的限制,其对进一步的化学修饰是相对惰性的。在这里,我们描述了Ac 3的快速平行微波辅助合成GalNAc-α-Bn衍生物可鉴定细胞O糖组学的多功能前体。总共成功合成了26种衍生物,包括荧光和生物正交反应性衍生物。评价前体作为T-合酶的受体的活性以及它们用作CORA前体的能力。具有几个有用的官能团前体的比AC更有效3的GalNAc-α-BN作为T-合酶受体和蜂窝O型糖组记者。这些前体将推动CORA技术用于功能性O糖组学的研究。
更新日期:2019-11-01
中文翻译:
用于细胞O-糖蛋白的多功能O-糖基前体的合成与表征。
蛋白质O-糖基化是一种普遍的翻译后修饰,在许多生物学过程中都起着至关重要的作用。最近,我们报道了技术称为蜂窝O型糖组记者/扩增(CORA)扩增和轮廓在全乙酰苄基α-的GalNAc(AC的存在下生长的活细胞粘蛋白型O-聚糖3的GalNAc-α-BN)。然而,CORA方法的应用和发展受到前体苄基糖苷配基的性质的限制,其对进一步的化学修饰是相对惰性的。在这里,我们描述了Ac 3的快速平行微波辅助合成GalNAc-α-Bn衍生物可鉴定细胞O糖组学的多功能前体。总共成功合成了26种衍生物,包括荧光和生物正交反应性衍生物。评价前体作为T-合酶的受体的活性以及它们用作CORA前体的能力。具有几个有用的官能团前体的比AC更有效3的GalNAc-α-BN作为T-合酶受体和蜂窝O型糖组记者。这些前体将推动CORA技术用于功能性O糖组学的研究。