Polymerization of amino acids containing nucleotide bases

Cheikh, Azzouz Ben; Orgel, Leslie E.

doi:10.1007/bf02101885

Cited by 10 publications

(3 citation statements)

References 12 publications

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“…Ethylenediamine dihydrochloride, carbonyldiimidazole (CDI), and, unless otherwise noted, amino acids, nucleosides, and nucleotides were obtained from commercial source. Amino acids containing nucleoside bases (I and II; Scheme 1) were a gift from Dr. Azzouz Ben Cheikh (Ben Cheikh and Orgel 1990 atives using polynucleotide kinase and 5'-[~2p]-ATP (Maniatis et al 1982). Ethylenediamine was attached to p(dT)10 and p(dT)t5 via a phosphoramidate bond using a published procedure (Chu and Orgel 1985) and purified by electrophoresis on an 8 M urea-20% polyacrylamide gel (32 V/cm).…”

Section: Methodsmentioning

confidence: 99%

The use of gel electrophoresis to study the reactions of activated amino acids with oligonucleotides

Zieboll

Orgel

1994

J Mol Evol

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We have used gel electrophoresis to study the primary covalent addition of amino acids to oligonucleotides or their analogs and the subsequent addition of further molecules of the amino acids to generate peptides covalently linked to the oligonucleotides. We have surveyed the reactions of a variety of amino acids with the phosphoramidates derived from oligonucleotide 5'-phosphates and ethylenediamine. We find that arginine and amino acids that can interact with oligonucleotides through stacking interactions react most efficiently. D- and L-amino acids give indistinguishable families of products.

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Section: Methodsmentioning

confidence: 99%

The use of gel electrophoresis to study the reactions of activated amino acids with oligonucleotides

Zieboll

Orgel

1994

J Mol Evol

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“…Willardiine was first identified by Rolf Gimelin in 1959 from the extracts of seeds of Acacia willardiana [ 1 ]. Structurally it corresponds to (2S)-2-amino-3-(2,4-dioxopyrimidin-1-yl)propanoic acid ( 1 , Figure 1 ) and carrying an uracil moiety it can be ascribed to the category of nucleoamino acids [ 2 , 3 , 4 ]. Willardiine is synthesized by the single specific enzyme uracilylalanine synthase, and the N–heterocyclic moiety uracil obtained by the orotate pathway [ 5 ] proved to be an effective bioisostere for the distal carboxyl group of L-glutamate [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

Willardiine and Its Synthetic Analogues: Biological Aspects and Implications in Peptide Chemistry of This Nucleobase Amino Acid

et al. 2022

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Willardiine is a nonprotein amino acid containing uracil, and thus classified as nucleobase amino acid or nucleoamino acid, that together with isowillardiine, forms the family of uracilylalanines isolated more than six decades ago in higher plants. Willardiine acts as a partial agonist of ionotropic glutamate receptors and more in particular it agonizes the non-N-methyl-D-aspartate (non-NMDA) receptors of L-glutamate: ie. the α-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) and kainate receptors. Several analogues and derivatives of willardiine have been synthesised in the laboratory in the last decades and these compounds show different binding affinities for the non-NMDA receptors. More in detail, the willardiine analogues have been employed not only in the investigation of the structure of AMPA and kainate receptors, but also to evaluate the effects of receptor activation in the various brain regions. Remarkably, there are a number of neurological diseases determined by alterations in glutamate signaling, and thus, ligands for AMPA and kainate receptors deserve attention as potential neurodrugs. In fact, similar to willardiine its analogues often act as agonists of AMPA and kainate receptors. A particular importance should be recognized to willardiine and its thymine-based analogue AlaT also in the peptide chemistry field. In fact, besides the naturally-occurring short nucleopeptides isolated from plant sources, there are different examples in which this class of nucleoamino acids was investigated for nucleopeptide development. The applications are various ranging from the realization of nucleopeptide/DNA chimeras for diagnostic applications, and nucleoamino acid derivatization of proteins for facilitating protein-nucleic acid interaction, to nucleopeptide-nucleopeptide molecular recognition for nanotechnological applications. All the above aspects on both chemistry and biotechnological applications of willardine/willardine-analogues and nucleopeptide will be reviewed in this work.

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“…It has also been proposed that a pre-RNA may have completely lacked sugar/s 17 and even phosphates 18 and thus a linear, achiral polymer conjugated to nitrogen heterocycles might represent a more realistic prebiotic ( pre-RNA) organic molecule capable of assembling and recognizing a distinct "partner". [19][20][21][22] Apart from their therapeutic potential, 23,24 acyclic nucleic acid analogues have been proposed as candidates for the prebiotic, pre-RNA world. [25][26][27][28][29][30] Herein, we report the synthesis and biophysical evaluation of an achiral, acyclic nucleic acid analogue, named DEANA i.e.…”

Section: Introductionmentioning

confidence: 99%

Achiral, acyclic nucleic acids: synthesis and biophysical studies of a possible prebiotic polymer

et al. 2015

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The search for prebiotic, nucleic acid precursors is, at its best, a speculative undertaking. Given the complex structure of RNA, it is not very likely that RNA was the first information system in the universe and thus finding possible precursor/s i.e. pre-RNA remains an open challenge. We, in this paper, have tried to construct nucleic acid polymers with a simple acyclic, achiral backbone. Such a linear, achiral backbone may have been formed from simple monomers that may have existed in the "prebiotic soup". We have shown that such polymers are capable of identifying the complementary "other self" and thus forming a potential system for information storage and transmission. This study thus involves investigation of nucleic acid analogues with a modified backbone that are likely to have formed in the prebiotic setting.

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Polymerization of amino acids containing nucleotide bases

Cited by 10 publications

References 12 publications

The use of gel electrophoresis to study the reactions of activated amino acids with oligonucleotides

The use of gel electrophoresis to study the reactions of activated amino acids with oligonucleotides

Willardiine and Its Synthetic Analogues: Biological Aspects and Implications in Peptide Chemistry of This Nucleobase Amino Acid

Achiral, acyclic nucleic acids: synthesis and biophysical studies of a possible prebiotic polymer

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