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Pseudouridine and N1-Methylpseudouridine Display pH-Independent Reaction Rates with Bisulfite Yielding Ribose Adducts
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-12 , DOI: 10.1021/acs.orglett.2c02427
Aaron M Fleming 1 , Songjun Xiao 1 , Cynthia J Burrows 1
Affiliation  

In RNA, pseudouridine (Ψ) and 5-methylcytidine (m5C) are located by their differential reactions with NaHSO3 at pH 5. The pyrimidines were allowed to react with NaHSO3, NaN3, NaCN, or NaSCN at pH 5 to find that NaHSO3 was unique in achieving quantitative yields. Pseudouridine reaction selectivity with NaHSO3 was found at pH 7 supported by the reaction rate constants. The Ψ derivative N1-methylpseudouridine found in mRNA vaccines reacts similarly with bisulfite to yield ribose adducts.

中文翻译:

假尿苷和 N1-甲基假尿苷与亚硫酸氢盐产生核糖加合物的反应速率与 pH 无关

在 RNA 中,假尿苷 ( Ψ ) 和 5-甲基胞苷 ( m 5 C ) 通过它们在 pH 5 下与 NaHSO 3的差异反应来定位。使嘧啶在 pH 5 下与 NaHSO 3、NaN 3、NaCN 或 NaSCN 反应,以发现 NaHSO 3在实现定量产率方面是独一无二的。发现pH 7 时与NaHSO 3的假尿苷反应选择性得到反应速率常数的支持。mRNA 疫苗中发现的Ψ衍生物N1-甲基假尿苷与亚硫酸氢盐发生类似反应,产生核糖加合物。
更新日期:2022-08-12
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