Synthesis of (3R,6R)- and (3S,6R)-piperidinone PNA

Püschl, Ask; Boesen, Thomas; Tedeschi, Tullia; Dahl, Otto; Nielsen, Peter E.

doi:10.1039/b103901f

Cited by 15 publications

(12 citation statements)

References 24 publications

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“…18e) inserted at the C-teminus. 171 PNAs derived from piperidinone 172 ( Fig. 18f) were also reported, though the rigidity of the ring and their particular geometry led to a decreased PNA:DNA duplex stability; however, the best performing was the (3R,6R)-isomer, which is in line with the proper group arrangement proposed earlier.…”

Section: Acyclic Chiral Pnassupporting

confidence: 50%

Chirality as a tool in nucleic acid recognition: Principles and relevance in biotechnology and in medicinal chemistry

et al. 2007

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The understanding of the interaction of chiral species with DNA or RNA is very important for the development of new tools in biology and of new drugs. Several cases in which chirality is a crucial point in determining the DNA binding mode are reviewed and discussed, with the aim of illustrating how chirality can be considered as a tool for improving the understanding of mechanisms and the effectiveness of nucleic acid recognition. The review is divided into two parts: the former describes examples of chiral species interacting with DNA: intercalators, metal complexes, and groove binders; the latter part is dedicated to chirality in DNA analogs, with discussion of phosphate stereochemistry and chirality of ribose substitutes, in particular of peptide nucleic acids (PNAs) for which a number of works have been published recently dealing with the effect of chirality in DNA recognition. The discussion is intended to show how enantiomeric recognition originates at the molecular level, by exploiting the enormous progresses recently achieved in the field of structural characterization of complexes formed by nucleic acid with their ligands by crystallographic and spectroscopic methods. Examples of application of the DNA binding molecules described and the role of chirality in DNA recognition relevant for biotechnology or medicinal chemistry are reported.

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Section: Acyclic Chiral Pnassupporting

confidence: 50%

Chirality as a tool in nucleic acid recognition: Principles and relevance in biotechnology and in medicinal chemistry

et al. 2007

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“…PNAs derived from piperidinone [101] [ Fig. (9b)] were also reported, though the rigidity of the ring and their particular geometry led to a decrease of PNA:DNA duplex stability; however, the best performing was the (3R,6R)-isomer, which is in line with proper group arrangement proposed above.…”

Section: Dna Binding By Cyclic Pnassupporting

confidence: 55%

Peptide Nucleic Acids with a Structurally Biased Backbone: Effects of Conformational Constraints and Stereochemistry

Corradini¹,

Sforza²,

Tedeschi³

et al. 2007

CTMC

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Peptide nucleic acids (PNAs) are polyamidic oligonucleotide analogs which have been described for the first time fifteen years ago and were immediately found to be excellent tools in binding DNA and RNA for diagnostics and gene regulation. Their use as therapeutic agents have been proposed since early studies and recent advancements in cellular delivery systems, and in the so called anti-gene strategy, makes them good candidates for drug development. The search for new chemical modification of PNAs is a very active field of research and new structures are continuously proposed. This review focuses on the recent advancements obtained by the modification of the PNA backbone, and their possible use in medicinal chemistry. In particular two classes of structurally biased PNAs are described in details: i) PNAs with acyclic structures and their helical preference, which is regulated by stereochemistry and ii) cyclic PNAs with preorganized structures, whose performances depend both on stereochemistry and on conformational constraints. The properties of these compounds are discussed in terms of affinity for nucleic acids, and several recent examples of their use in cellular or animal systems are presented.

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“…This is interesting since in an earlier study 12 it had been remarked that the sixmembered piperidine rings are unlikely to stabilize the derived PNA structures for complex formation. In the present aepipPNA analogues the stereochemical dispositions of substituents seem to lead to a favorable preorganization of PNA backbone for the formation of stable triplexes with DNA.…”

Section: Uv-t M Studies On Pna 2 -Dna Triplexesmentioning

confidence: 94%

“…This has triggered interest in six-membered PNA analogs, 11 although with some initial misgivings. 12 Recently, we reported the synthesis of chimeric PNAs, in which one of the isomers (2S,5R) of aminoethylpipecolyl PNA, aepipPNA IV, 13 was introduced at pre-determined sites of the oligomers. This six-membered homologue of aepPNA is derived by bridging the a 0 -C atom of the glycyl unit and the b 0 -C atom of linker to nucleobase in PNA with an ethylene bridge instead of a methylene bridge in III.…”

Section: Introductionmentioning

confidence: 99%

(2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: synthesis and duplex/triplex stability

2004

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Synthesis of (3R,6R)- and (3S,6R)-piperidinone PNA

Cited by 15 publications

References 24 publications

Chirality as a tool in nucleic acid recognition: Principles and relevance in biotechnology and in medicinal chemistry

Chirality as a tool in nucleic acid recognition: Principles and relevance in biotechnology and in medicinal chemistry

Peptide Nucleic Acids with a Structurally Biased Backbone: Effects of Conformational Constraints and Stereochemistry

(2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: synthesis and duplex/triplex stability

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