Synthesis of 2-Aminopyridine-Modified Peptide Nucleic Acids

被引：2

作者：

Kumpina, Ilze ^{[1
,2
]}

Baskevics, Vladislavs ^{[2
]}

Walby, Grant D. ^{[3
]}

Tessier, Brandon R. ^{[1
]}

Saei, Sara Farshineh ^{[1
]}

Ryan, Christopher A. ^{[1
]}

Mackay, James A. ^{[3
]}

Katkevics, Martins ^{[2
]}

Rozners, Eriks ^{[1
]}

机构：

[1] Binghamton Univ, SUNY, Dept Chem, Binghamton, NY 13902 USA

[2] Latvian Inst Organ Synth, Aizkraukles 21, LV-1006 Riga, Latvia

[3] Elizabethtown Coll, Dept Chem & Biochem, Elizabethtown, PA 17022 USA

来源：

SYNLETT | 2024年 / 35卷 / 06期

基金：

美国国家科学基金会;

关键词：

peptide nucleic acids; aminopyridine; RNA recognition; triple helix; solid-phase synthesis; SEQUENCE-SELECTIVE RECOGNITION; TRIPLE-HELICAL RECOGNITION; BASE-PAIRS; RNA; DNA; PSEUDOISOCYTOSINE; NUCLEOBASE; BINDING; PNA; NUCLEOSIDES;

D O I：

10.1055/a-2191-5774

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triplex-forming peptide nucleic acids (PNAs) require chemical modifications for efficient sequence-specific recognition of DNA and RNA at physiological pH. Our research groups have developed 2-amino pyridine (M) as an effective mimic of protonated cytosine in C+center dot G-C triplets. M-modified PNAs have a high binding affinity and sequence specificity as well as promising biological properties for improving PNA applications. This communication reports the optimization of synthetic procedures that give PNA M monomer in seven steps, with minimal need for column chromatography and in good yields and high purity. The optimized route uses inexpensive reagents and easily performed reactions, which will be useful for the broad community of nucleic acid chemists. Thought has also been given to the potential for future development of industrial syntheses of M monomers.

引用

页码：649 / 653

页数：5

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