Phosphonic Ester Nucleic Acids (PHONAs): Oligonucleotide Analogues with an Achiral Phosphonic Acid Ester Backbone

Peyman, Anusch; Uhlmann, Eugen; Wagner, Konrad; Augustin, Sascha; Breipohl, Gerhard; Will, David W.; Schäfer, Andrea; Wallmeier, Holger

doi:10.1002/anie.199626361

Cited by 42 publications

(14 citation statements)

References 23 publications

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“…Peptides that carry nucleobases along main chains have been utilized as surrogates of nucleic acids 1–25. Peptide nucleic acids show higher affinity to nucleic acids than nucleic acids themselves because of the absence of repulsive forces between negative charges and do not suffer attacks from nucleases and proteases in vivo and in vitro.…”

Section: Introductionmentioning

confidence: 99%

Transitional cell carcinoma of renal allograft associated with BK virus infection

Saquib

Barri

Saad

et al. 2009

Dialysis & Transplantation

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A new series of oxy‐peptide nucleic acids (pyrrolidine‐based oxy‐peptide nucleic acids = POPNAs) of four different stereoisomeric forms (cis‐L, cis‐D, trans‐L, trans‐D) have been synthesized. To find a favorable stereoisomer of POPNA for hybridization with DNA or RNA, thermodynamic parameters and conformations of the hybrids between the four stereoisomers with 9 adenine bases [po(A9)s] and dT9 or rU9 were investigated from ultraviolet (UV) melting curves and circular dichroism (CD) spectra. The cis‐L‐po(A9) formed the most stable hybrid with dT9, because of the smallest entropy loss, despite the smallest enthalpy gain. In contrast, trans‐L‐po(A9) formed the most stable hybrid with rU9, because of the largest enthalpy gain, despite the largest entropy loss. The hybrid stability of trans‐L‐po(A9) with rU9 was significantly improved as compared with a previous version of oxy‐peptide nucleic acid (OPNA) that lacks the pyrrolidine ring. © 2005 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 84: 267–273, 2006 This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com

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Section: Introductionmentioning

confidence: 99%

Transitional cell carcinoma of renal allograft associated with BK virus infection

Saquib

Barri

Saad

et al. 2009

Dialysis & Transplantation

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“…One of the first attempts to directly address the issue of solubility was described by Peyman and co-workers where they attempted to synthesise a PNA analogue, termed phosphonic-ester nucleic acid or pPNA (Peyman et al, 1996) without compromising the binding properties of PNA. Here, the standard achiral and neutral N-(2-aminoethy1)-glycine PNA backbone is replaced with an achiral and negatively charged backbone where the nucleobases are attached through carboxymethylene linkers.…”

Section: The Many Flavours Of Artificial Nucleic Acids; Different Strmentioning

confidence: 99%

Artificial Nucleic Acid Probes and Their Applications in Clinical Microbiology

Singer

Tang

2015

Methods in Microbiology

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“…Phosphonic acid esters are also used in the rapidly developing area of biochemistry. The synthesis of oligonucleotide analogues with an achiral phosphonic acid ester backbone has been carried out (Peyman et al, 1996). Aminophosphonic acid and its derivatives are commonly known as potential enzyme inhibitors (Beers et al, 1996;Pawełczak et al, 1998;Vovk et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

Two closely related {4-[(N-substituted amino)(diethoxyphosphoryl)methyl]phenyl}boronic acids

Zhang

et al. 2017

Acta Crystallogr C

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Organic phosphonic acids and organic phosphonic acid esters have been of much interest due to their applications in the fields of medicine, agriculture and industrial chemistry. Boronic acids can act as synthetic intermediates and building blocks and are used in sensing, protein manipulation, therapeutics, biological labelling and separation. The additional introduction of an aminophosphonic acid group into a boronic acid may give new opportunities for application. To study the structure of such multifunctional compounds, we prepared two new derivatives which can be easily converted to the corresponding phosphonic acids. In the title compounds, {4-[(butylamino)(diethoxyphosphoryl)methyl]phenyl}boronic acid monohydrate, CHBNOP·HO, (I), and {4-[(diethoxyphosphoryl)(4-nitroanilino)methyl]phenyl}boronic acid, CHBNOP, (II), three different substituents are attached to a central C-H group, namely 4-boronophenyl, diethoxyphosphoryl and amine. Compound (I) crystallizes as a monohydrate and O-H...N hydrogen bonds link neighbouring molecules into chains along the [001] direction. The solvent water molecule connects two such chains running in opposite directions. Compound (II) crystallizes as an ansolvate and classical hydrogen bonds result in a layer structure in the (001) plane.

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Phosphonic Ester Nucleic Acids (PHONAs): Oligonucleotide Analogues with an Achiral Phosphonic Acid Ester Backbone

Cited by 42 publications

References 23 publications

Transitional cell carcinoma of renal allograft associated with BK virus infection

Transitional cell carcinoma of renal allograft associated with BK virus infection

Artificial Nucleic Acid Probes and Their Applications in Clinical Microbiology

Two closely related {4-[(N-substituted amino)(diethoxyphosphoryl)methyl]phenyl}boronic acids

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