Synthesis, purification and characterization of two peptide-oligonucleotide conjugates as potential artificial nucleases

Truffert, Jean-Christophe; Asseline, Ulysse; Brack, Andrè; Thuong, Nguyen T.

doi:10.1016/0040-4020(96)00018-x

Cited by 50 publications

(50 citation statements)

References 45 publications

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“…In principle, removal of the Boc group on a solid support can be accomplished with a 10% TFA solution after automated synthesis [37]. However, it has been shown that such a TFA treatment can lead to a certain amount of depurination of the oligonucleotide [34,38]. The research groups of Gait and Herdewijn both proved that removal of the Boc group from imidazole during standard deprotection procedures with saturated methanolic ammonia after oligonucleotide synthesis is possible [35,39], therefore in our second attempt, using urocanic acid (1), the imidazole moiety was Boc-protected using di-tert-butyldicarbonate as shown in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…However, the DNP protection did not survive conditions used during purification of the final DMTr-protected nucleoside. Because it has further been proven that the DNP group gives yellow contaminated products after deprotection, we decided to change the protecting group into a tert-butoxycarbonyl (Boc) one [34], which is compatible with the reagents used during nucleoside-and oligonucleotide synthesis [35][36][37]. In principle, removal of the Boc group on a solid support can be accomplished with a 10% TFA solution after automated synthesis [37].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

Catry

Madder

2007

Molecules

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

Catry

Madder

2007

Molecules

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“…Truffert et al used this approach to prepare the ODN-peptide conjugate 17 that can act as artificial nuclease (Fig. 6) [36]. The peptide was assembled on CPG support 14 using pentafluorophenylactivated ester of amino acids.…”

Section: Step-wise Solid-phase Synthesismentioning

confidence: 99%

Chemical Strategies for Oligonucleotide-Conjugates Synthesis

Defrancq

Singh²,

Spinelli

2008

COC

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Oligonucleotide conjugates have found numerous applications in the field of diagnostics and therapeutics. Structurally diverse oligonucleotide conjugates have been prepared and evaluated for various applications. Research efforts have focused on the development of synthetic procedures to accomplish efficient oligonucleotide conjugation with different target molecules. Both on-support and solution-phase coupling procedures have been used to conjugate oligonucleotides. This review gives an account of major synthetic approaches available to prepare covalent oligonucleotide conjugates with diverse target molecules.

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“…Upon metal binding, these systems can be activated toward the oxidative modification of an associated substrate, e.g ., nucleic acid strand scission or protein cleavage/crosslinking [1]. Indeed, the discovery of their ability to effect the oxidative modification of substrates [4,5] has led to the exploitation of these tripeptides as synthetic [6–9] or biosynthetic [10,11] conjugates to DNA-targeted proteins and a range of additional biomolecules including peptides [12], low molecular weight drugs [13–15], oligonucleotides [16,17], PNA strands [18], and protein-targeted systems [19–22]. More recently, Gly-Gly-His has provided a basis for the development of catalytic metallodrugs [23, 24].…”

Section: Introductionmentioning

confidence: 99%

DNA Cleaving “Tandem-Array” Metallopeptides Activated With KHSO<sub>5</sub>: Towards the Development of Multi-Metallated Bioactive Conjugates and Compounds

Lewis

Williams

Fang

et al. 2014

CBC

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Amino terminal peptides of the general form Gly-Gly-His have been used to introduce single sites of metal binding and redox activity into a wide range of biomolecules to create bioactive compounds and conjugates capable of substrate oxidation. We report here that Gly-Gly-His-like peptides linked in a tandem fashion can also be generated leading to multi-metal binding arrays. While metal binding by the native Gly-Gly-His motif (typically to Cu2+, Ni2+, or Co2+) requires a terminal peptide amine ligand, previous work has demonstrated that an ornithine (Orn) residue can be substituted for the terminal Gly residue to allow solid-phase peptide synthesis to continue via the side chain N-δ. This strategy thus frees the Orn residue N-α for metal binding and permits placement of a Gly-Gly-His-like metal binding domain at any location within a linear, synthetic peptide chain. As we show here, this strategy also permits the assembly of tandem arrays of metal binding units in linear peptides of the form: NH2-Gly-Gly-His-[(δ)-Orn-Gly-His]n-(δ)-Orn-Gly-His-CONH2 (where n = 0, 1, and 2). Metal binding titrations of these tandem arrays monitored by UV-vis and ESI-MS indicated that they bind Cu2+, Ni2+, or Co2+ at each available metal binding site. Further, it was found that these systems retained their ability to modify DNA oxidatively and to an extent greater than their parent M(II)•Gly-Gly-His. These findings suggest that the tandem array metallopeptides described here may function with increased efficiency as “next generation” appendages in the design of bioactive compounds and conjugates.

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Synthesis, purification and characterization of two peptide-oligonucleotide conjugates as potential artificial nucleases

Cited by 50 publications

References 45 publications

Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

Synthesis of Functionalised Nucleosides for Incorporation into Nucleic Acid-Based Serine Protease Mimics

Chemical Strategies for Oligonucleotide-Conjugates Synthesis

DNA Cleaving “Tandem-Array” Metallopeptides Activated With KHSO<sub>5</sub>: Towards the Development of Multi-Metallated Bioactive Conjugates and Compounds

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