New Strategy for the Synthesis of 3′,5′‐Bifunctionalized Oligonucleotide Conjugates through Sequential Formation of Chemoselective Oxime Bonds

Edupuganti, Om Prakash; Singh, Yashveer; Defrancq, Éric; Dumy, Pascal

doi:10.1002/chem.200400390

Cited by 48 publications

(38 citation statements)

References 56 publications

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“…[18] Thus, the ODN-3'-Lys-Trp-Lys (with the tripeptide attached to the 3' end of the ODN) and Lys-Trp-Lys-5'-ODN (with the tripeptide Lys-Trp-Lys linked to the 5' end of the complementary ODN) were prepared by using the oxime coupling reaction according to previously reported methods. [38,39] Briefly, the 3' conjugate was prepared by treating the ODN ( 5' TAAATT TAATAA AAAAAX 3 , X represents the aldehyde containing linker) with the Lys-Trp-Lys tripeptide containing the oxyamino group at the N terminus in ammonium acetate buffer (0.4 m), overnight, at room temperature. The same method was applied for the synthesis of the 5' conjugate functionalized with the Lys-Trp-Lys peptide.…”

Section: Methodsmentioning

confidence: 99%

Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by Ru^II–TAP Complexes

Ghesquière

Gauthier

Winter

et al. 2011

Chemistry A European J

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Ru(II)-TAP complexes have been shown to be very attractive compounds in the frame of developments of new anticancer drugs targeting the genetic material. This increasing interest originates from observations of covalent bond formations, triggered by photo-induced electron transfer (PET) between Ru(II)-TAP complexes and guanine bases of DNA. This photoreaction has recently been extended to the tryptophan (Trp) amino acid for future applications involving peptides. Thus, a double photo-addition of Trp residues of peptides on Ru(II) complexes is demonstrated by mass spectrometry with some structural issues. Such bi-adduct formations offer the possibility of photocrosslinking two Trp-containing biomolecules, which is investigated in this study. Thus, photocrosslinking between two complementary oligonucleotides (ODNs) derivatized by Trp-containing tripeptides is demonstrated by polyacrylamide gel electrophoresis (PAGE) in the presence of Ru(II)-TAP complexes. Both PAGE and MS indicate that such photocrosslinkings arise from two reaction pathways: either via the double addition of Trp residues on the Ru complex or from dimerization of Trp radicals. The competition between these two pathways depends on the experimental conditions. Heterobridgings between guanine bases and tryptophan residues mediated by Ru(II)-TAP complexes is also examined, opening the way to ODN-peptide photocrosslinkings.

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Section: Methodsmentioning

confidence: 99%

Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by Ru^II–TAP Complexes

Ghesquière

Gauthier

Winter

et al. 2011

Chemistry A European J

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“…Treatment of the oligonucleotide aldehyde 19 with aminooxysugar 20 leads to the formation of oxime ethers (Scheme 8) very efficiently in aqueous solution at pH 4.6. The oxime linkages are stable at pH 7.0 for over 72 h. Using this approach, 3′,5′-bisconjugation through an oxime bond formation was achieved [107,108].…”

Section: Oximationmentioning

confidence: 97%

Glycotargeting to improve cellular delivery efficiency of nucleic acids

Yan

Tram

2007

Glycoconj J

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Nucleic acids bearing glycans of various structures have been under vigorous investigation in the past decade. The carbohydrate moieties of such complexes can serve as recognition sites for carbohydrate-binding proteins-lectins-and initiate receptor-mediated endocytosis. Therefore, carbohydrates can enhance cell targeting and internalization of nucleic acids that are associated with them and thus improve the bioavailability of nucleic acids as therapeutic agents. This review summarizes nucleic acid glycosylation in nature and approaches for the preparation of both non-covalently associated and covalently-linked carbohydrate-nucleic acid complexes.

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“…[33][34][35]39,40] Accordingly, d-biotin and N-(4-methoxytrityl)-1,4-phenylenedimethanamine [41] (17) were first coupled by 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) activation to obtain 18. Besides biotin, the ligand contained a 1,4-phenylene chromophore and a Boc-protected aminooxy function.…”

Section: Synthesis Of the Biotin Ligand 19mentioning

confidence: 99%

Synthesis of Biotinylated Multipodal Glycoclusters on a Solid Support

et al. 2012

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Trivalent glycoconjugates, each bearing a biotin side arm in addition to three different sugar ligands, have been synthesized on a solid support. The conjugates were assembled on an orthogonally protected pentaerythrityl tetramine core that was anchored to the support through a backbone amide linker. Peptide coupling chemistry was applied to elongate three of the branches with β‐alanine and a fully acylated glycosylacetic acid. The fourth branch was levulinoylated and oximated with aminooxy‐derivatized D‐biotin, followed by acidolytic release into solution. The acyl protecting groups were removed by methoxide‐catalyzed transesterification in methanol.

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New Strategy for the Synthesis of 3′,5′‐Bifunctionalized Oligonucleotide Conjugates through Sequential Formation of Chemoselective Oxime Bonds

Cited by 48 publications

References 56 publications

Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by Ru^II–TAP Complexes

Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by Ru^II–TAP Complexes

Glycotargeting to improve cellular delivery efficiency of nucleic acids

Synthesis of Biotinylated Multipodal Glycoclusters on a Solid Support

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New Strategy for the Synthesis of 3′,5′‐Bifunctionalized Oligonucleotide Conjugates through Sequential Formation of Chemoselective Oxime Bonds

Cited by 48 publications

References 56 publications

Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by RuII–TAP Complexes

Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by RuII–TAP Complexes

Glycotargeting to improve cellular delivery efficiency of nucleic acids

Synthesis of Biotinylated Multipodal Glycoclusters on a Solid Support

Contact Info

Product

Resources

About

Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by Ru^II–TAP Complexes

Photocrosslinking between Peptide–Peptide or Peptide–Oligonucleotide by Ru^II–TAP Complexes