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

Shirude, Pravin S.; Kumar, Vaijayanti A.; Ganesh, Krishna N.

doi:10.1016/j.tet.2004.07.080

Cited by 18 publications

(13 citation statements)

References 27 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: 82%

“…An example of the behavior of two stereoisomers of a six-membered ring PNA is the discrimination between the parallel versus antiparallel DNA reported for a single modified (2S,5R)-aminoethylpipecolic PNA unit 171 inserted in the middle of the strand. The effect is highly dependent on the position of the stereocenters, as described for flexible chiral PNAs; DNA binding through triplex formation was found to be stronger in the case of the (2R,5S)-monomer (Fig.…”

Section: Acyclic Chiral Pnasmentioning

confidence: 99%

See 1 more Smart Citation

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: 82%

Section: Acyclic Chiral Pnasmentioning

confidence: 99%

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

et al. 2007

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“…Cyclisation of diazo compounds derived from α-amino acids using either rhodium or ruthenium complexes have allowed the synthesis of 5-oxopipecolic acids in good yields. 20,21 Ganesh and co-workers prepared diazoketone 29 under standard conditions from the orthogonally protected glutamic acid derivative 28 in 65% yield (Scheme 5). 20 In contrast to previous examples that have used the cyclisation of linear amino acids to form the pipecolic acid ring, methods have also been developed involving ring expansion of cyclic amino acids.…”

Section: Scheme 1 Synthesis Of (2s3r)-3-hydroxypipecolic Acid 12 Bymentioning

confidence: 99%

Asymmetric Synthesis of Pipecolic Acid and Derivatives

Cant

Sutherland

2012

Synthesis

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The nonproteinogenic α-amino acid, L-pipecolic acid and its derivatives are components of a wide range of pharmacologically active compounds. The significant biological activity of these compounds has resulted in the development of many synthetic approaches for their preparation. This review highlights these key methods as well as the application of these compounds for the preparation of enzyme inhibitors, conformationally restricted building blocks and peptidomimetics.

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“…An example of the behaviour of two stereoisomers of a 6-membered ring PNA is the discrimination between the parallel versus antiparallel DNA reported for a single modified (2S,5R) amino-ethyl pipecolic PNA unit [100] [Fig. (9a)] inserted in the middle of the strand.…”

Section: Dna Binding By Cyclic Pnasmentioning

confidence: 99%

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

Cited by 18 publications

References 27 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

Asymmetric Synthesis of Pipecolic Acid and Derivatives

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

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