Expedient and generic synthesis of imidazole nucleosides by enzymatic transglycosylation

被引:17
作者
Vichier-Guerre, S. [1 ]
Dugue, L. [1 ]
Bonhomme, F. [1 ]
Pochet, S. [1 ]
机构
[1] Inst Pasteur, CNRS, UMR3523, Unite Chim & Biocatalyse, 28 Rue Dr Roux, F-75724 Paris, France
关键词
LACTOBACILLUS-HELVETICUS; N-DEOXYRIBOSYLTRANSFERASES; PURINE NUCLEOSIDES; BASE-PAIRS; ANALOGS; DNA; RECOGNITION; DESIGN; PHOSPHORYLASES; BIOTECHNOLOGY;
D O I
10.1039/c6ob00405a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward route to original imidazole-based nucleosides that makes use of an enzymatic N-trans-glycosylation step is reported in both the ribo-and deoxyribo-series. To illustrate the scope of this approach, a diverse set of 4-aryl and 4-heteroaryl-1H-imidazoles featuring variable sizes and hydrogen-bonding patterns was prepared using a microwave-assisted Suzuki-Miyaura cross-coupling reaction. These imidazole derivatives were examined as possible substrates for the nucleoside 2'-deoxyribosyltransferase from L. leichmannii and the purine nucleoside phosphorylase from E. coli. The optimum trans-glycosylation conditions, including the use of co-adjuvants to address solubility issues, were defined. Enzymatic conversion of 4-(hetero)arylimidazoles to 2'-deoxyribo- or ribo-nucleosides proceeded in good to high conversion yields, except bulky hydrophobic imidazole derivatives. Nucleoside deoxyribosyltransferase of class II was found to convert the widest range of functionalized imidazoles into 2'-deoxy-ribonucleosides and was even capable of bis-glycosylating certain heterocyclic substrates. Our findings should enable chemoenzymatic access to a large diversity of flexible nucleoside analogues as molecular probes, drug candidates and original building blocks for synthetic biology.
引用
收藏
页码:3638 / 3653
页数:16
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