An improved synthesis of guanosine TNA phosphoramidite for oligonucleotide synthesis

被引：0

作者：

Majumdar, Biju ^{[1
]}

Sarma, Daisy ^{[1
]}

Lee, Erica M. ^{[1
]}

Setterholm, Noah A. ^{[1
]}

Chaput, John C. ^{[1
,2
,3
,4
]}

机构：

[1] Univ Calif Irvine, Dept Pharmaceut Sci, Irvine, CA 92697 USA

[2] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

[3] Univ Calif Irvine, Dept Mol Biol & Biochem, Irvine, CA 92697 USA

[4] Univ Calif Irvine, Dept Chem & Biomol Engn, Irvine, CA USA

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2024年

关键词：

Threose nucleic acid; phosphoramidites; coupling efficiency; solid-phase oligonucleotide synthesis; PROGRESS; RNA;

D O I：

10.1080/15257770.2024.2369688

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The chemical synthesis of guanosine nucleosides generates both the N9 and N7 regioisomers, which require careful separation to obtain the desired N9 isomer. To preferentially obtain the N9 isomer, a bulky diphenylcarbamoyl (DPC) group can be installed at the O6 position of guanine. However, installation of the DPC group presents a challenging task due to low solubility of the N-acetyl protected guanine. Here we report the usage of commercially available 2-amino-6-chloro purine as a new strategy that offers a more efficient route to the synthesis of the guanine phosphoramidite of threose nucleic acid (TNA).

引用

页数：12

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