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Selective acylation of ribonucleotides and ribonucleosides with acylimidazoles
Author(s) -
Yu Wang,
YaoZhong Xu,
ZaiWan Yang,
XiangYuan Liu,
QiWen Wang
Publication year - 1988
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19880060310
Subject(s) - chemistry , acylation , deoxyribonucleoside , derivative (finance) , uridine , organic chemistry , stereochemistry , biochemistry , catalysis , enzyme , rna , financial economics , economics , gene
Selective acylation of ribonucleotides and ribonucleosides can be achieved by using N ‐acylimidazole on a preparative scale with good yields (50–80%). For uridine 3′‐phosphate (Up): in the presence of MDCAI, the 2′‐ O ‐acyl‐derivative is the main product, while in the presence of an excess of TEAH, the 5′‐ O ‐acyl‐derivative is the main product. For ribonucleosides (U R or A R or ψ R ): in the presence of MDCAI, the acylations take place preferably at 2′‐OH or 3′‐OH of ribonucleosides and only 3′‐ O ‐acyl‐derivatives can be isolated by crystallization; in the presence of an excess of TEAH. 5′‐ O ‐acyl‐derivative is obtained as the main product. Arabinonucleoside and deoxyribonucleoside are only slowly acylated to form 5′‐ O ‐acyl‐derivatives as the main products by acylimidazole in the presence of MDCAI. Possible mechanisms of these acylations have been discussed.