Publication

Synthesis of Pyrrolidinone PNA: A Novel Conformationally Restricted PNA Analogue

2001
Journal Articles

Abstract

To preorganize PNA for duplex formation, a new cyclic pyrrolidinone PNA analog has been designed. In this analog the aminoethyl-glycine backbone and the methylene-carbonyl linker are connected, introducing two chiral centers compared to PNA. The four stereoisomers of the adenine analog were synthesized, and the hybridization properties of PNA decamers contg. one analog were measured against complementary DNA, RNA, and PNA strands. The (3S,5R) isomer was shown to have the highest affinity toward RNA, and to recognize RNA and PNA better than DNA. The (3S,5R ) isomer was used to prep. a fully modified decamer which bound to rU10 with only a small decrease in Tm (DTm/mod = 1 DegC) relative to aminoethyl-glycine PNA. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/3301f6b8-860e-4a09-8ce1-d52d080b9698

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2001
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3301f6b8-860e-4a09-8ce1-d52d080b9698

About this result

Related concepts (32)

Peptide nucleic acid

Peptide nucleic acid (PNA) is an artificially synthesized polymer similar to DNA or RNA. Synthetic peptide nucleic acid oligomers have been used in recent years in molecular biology procedures, diagnostic assays, and antisense therapies. Due to their higher binding strength, it is not necessary to design long PNA oligomers for use in these roles, which usually require oligonucleotide probes of 20–25 bases. The main concern of the length of the PNA-oligomers is to guarantee the specificity.

DNA

Deoxyribonucleic acid (diːˈɒksᵻˌraɪboʊnjuːˌkliːᵻk,_-ˌkleɪ-; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of all known organisms and many viruses. DNA and ribonucleic acid (RNA) are nucleic acids. Alongside proteins, lipids and complex carbohydrates (polysaccharides), nucleic acids are one of the four major types of macromolecules that are essential for all known forms of life.

Complementary DNA

In genetics, complementary DNA (cDNA) is DNA synthesized from a single-stranded RNA (e.g., messenger RNA (mRNA) or microRNA (miRNA)) template in a reaction catalyzed by the enzyme reverse transcriptase. cDNA is often used to express a specific protein in a cell that does not normally express that protein (i.e., heterologous expression), or to sequence or quantify mRNA molecules using DNA based methods (qPCR, RNA-seq). cDNA that codes for a specific protein can be transferred to a recipient cell for expression, often bacterial or yeast expression systems.

Related publications (1)

Synthesis of Pyrrolidinone PNA: A Novel Conformationally Restricted PNA Analogue

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Towards a total synthesis of aminoacylated t-RNAs