Multicomponent Synthesis of C(8)-Substituted Purine Building Blocks of Peptide Nucleic Acids from Prebiotic Compounds.

IF 2.5 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Eleonora Mancin, Eliana Capecchi, Lorenzo Botta, Bruno Mattia Bizzarri
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引用次数: 0

Abstract

We have explored the reaction of a three-components mixture of aminomalononitrile, urea and α-amino acid methyl esters for the multicomponent synthesis substituted purines resembling PNA's building blocks. 2,6-diamino-purines, 6-amino-3,9-dihydro-2H-purin-2-one (iso-guanines), and 3,9-dihydro-6H-purin-6-one derivatives, selectively decorated at C(8)-position of the purine ring with different amino acid residues, were obtained from acceptable to good yields. The regio-selectivity of the transformation was controlled by the use of urea in the ternary mixture and by the annulation agent involved in the ring-closure of amino-imidazole carbonitrile intermediates. Solvent free conditions, microwave irradiation and simple one-carbon containing reagents further satisfied the major requirement of atom economy and sustainable chemistry. Due to the prebiotic nature of the three-components mixture and of annulation agents, it also embodies the possibility for the synthesis of novel PNAs bearing purine nucleobases decorated at C(8)-position of the imidazole ring as alternative RNA analogues in molecular evolution.

用前生物化合物多组分合成肽核酸的 C(8)- 取代嘌呤基块。
我们探索了氨基丙二腈、尿素和 α-氨基酸甲酯三组份混合物的反应,用于多组分合成类似 PNA 构建模块的替代嘌呤。在嘌呤环的 C(8)位上用不同的氨基酸残基进行选择性装饰,获得了 2,6-二氨基嘌呤、6-氨基-3,9-二氢-2H-嘌呤-2-酮(异鸟嘌呤)和 3,9-二氢-6H-嘌呤-6-酮衍生物,产量可接受,甚至很高。转化的区域选择性受三元混合物中尿素的使用和氨基咪唑腈中间体窄环化过程中环化剂的控制。无溶剂条件、微波辐照和简单的含碳试剂进一步满足了原子经济和可持续化学的主要要求。由于三组分混合物和环化剂的前生物性质,它还体现了合成新型 PNA 的可能性,这些 PNA 含有在咪唑环 C(8)- 位上装饰的嘌呤核碱基,可作为分子进化中的替代 RNA 类似物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
ChemistryOpen
ChemistryOpen CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
4.80
自引率
4.30%
发文量
143
审稿时长
1 months
期刊介绍: ChemistryOpen is a multidisciplinary, gold-road open-access, international forum for the publication of outstanding Reviews, Full Papers, and Communications from all areas of chemistry and related fields. It is co-owned by 16 continental European Chemical Societies, who have banded together in the alliance called ChemPubSoc Europe for the purpose of publishing high-quality journals in the field of chemistry and its border disciplines. As some of the governments of the countries represented in ChemPubSoc Europe have strongly recommended that the research conducted with their funding is freely accessible for all readers (Open Access), ChemPubSoc Europe was concerned that no journal for which the ethical standards were monitored by a chemical society was available for such papers. ChemistryOpen fills this gap.
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