Synthesis of 4-Iodoimidazole Nucleosides: A Biocatalyzed Whole Cell Approach

IF 2.7 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2025-01-23 DOI:10.1002/ejoc.202400950
Lautaro A. M. Giaimo, Dr. Leticia Lafuente, Dr. Romina N. Fernández Varela, Dr. Matías L. Nóbile, Dr. Adolfo M. Iribarren, Dr. Elizabeth S. Lewkowicz
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Abstract

Nucleoside analogues are biologically active drugs that are well known for their therapeutic properties. Chemical synthesis of these compounds is complex due to time constraints, contaminant methodologies, and numerous steps involved. In contrast, biocatalyzed synthesis, particularly using microorganisms, offers many advantages. In this work, we introduce the synthesis of 4-iodoimidazole-ribonucleoside, through a microbial transglycosylation biocatalyzed by Erwinia amylovora whole cells, selected as the optimal catalyst for this biotransformation upon evaluating our microbial collection. Parameters were analyzed to optimize the reaction, and the use of this biocatalyst in transglycosylation with other natural and non-natural bases and different sugar donor nucleosides was also verified.

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4 -碘咪唑核苷的合成:生物催化全细胞方法
核苷类似物是生物活性药物,以其治疗特性而闻名。由于时间限制、污染物方法和涉及的众多步骤,这些化合物的化学合成是复杂的。相比之下,生物催化合成,特别是使用微生物,提供了许多优点。在这项工作中,我们介绍了4 -碘咪唑-核糖核苷的合成,通过微生物转糖基化的生物催化,通过评估我们的微生物收集被选为生物转化的最佳催化剂。对反应参数进行了优化,并验证了该生物催化剂与其他天然和非天然碱基以及不同糖供体核苷的转糖基化反应。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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