An Improved Approach for Practical Synthesis of 5-Hydroxymethyl-2'-deoxycytidine (5hmdC) Phosphoramidite and Triphosphate

5-Hydroxymethyl-2'-deoxycytidine (5hmdC) phosphoramidite and triphosphate are important building blocks in 5hmdC-containing DNA synthesis for epigenetic studies. However, efficient and practical methods for the synthesis of these compounds are still limited. The current research provides an int...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-01, Vol.27 (3), p.749
Main Authors: Yang, Dong-Zhao, Chen, Zhen-Zhen, Chi, Mei, Dong, Ying-Ying, Pu, Shou-Zhi, Sun, Qi
Format: Article
Language:English
Subjects:
5-hydroxymethyl-2′-deoxycytidine (5hmdC)
Ammonia
cyanoethyl ether
DNA biosynthesis
Epigenetics
Intermediates
P(V)-N activation
phosphoramidite
Reagents
triphosphate
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Summary:5-Hydroxymethyl-2'-deoxycytidine (5hmdC) phosphoramidite and triphosphate are important building blocks in 5hmdC-containing DNA synthesis for epigenetic studies. However, efficient and practical methods for the synthesis of these compounds are still limited. The current research provides an intensively improved synthetic method that enables the preparation of commercially available cyanoethyl-protected 5hmdC phosphoramidite with an overall yield of 39% on 5 g scale. On the basis of facile and efficient accesses to cyanoethyl protected-5hmdU and 5hmdC intermediates, two efficient synthetic routes for 5hmdC triphosphate were also developed.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27030749