Linking the 3′ Ends of Oligonucleotide Duplexes with Cystine Disulfide Bridges

Marchán, Vicente; Pulido, Daniel; Pedroso, Enrique; Grandas, Anna

doi:10.1002/ejoc.200500567

Cited by 5 publications

(5 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5'-Diene modified ODNs were prepared by incorporating moieties such as hexadiene and furan and reacted with maleimide derivatised biotin or fluorescein to obtain ODN-conjugates labelled with fluorescein or biotin. Grandas et al obtained ODN-peptide conjugates by reacting diene-modified ODN with maleimide-derivatised peptides in high purity and yield [151]. Häner et al used this approach to incorporate fluorescein label into the hairpin loop of an ODN [150].…”

Section: Conjugation Via Cycloaddition Reactionsmentioning

confidence: 99%

Chemical Strategies for Oligonucleotide-Conjugates Synthesis

Defrancq

Singh²,

Spinelli

2008

COC

View full text Add to dashboard Cite

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.

show abstract

Section: Conjugation Via Cycloaddition Reactionsmentioning

confidence: 99%

Chemical Strategies for Oligonucleotide-Conjugates Synthesis

Defrancq

Singh²,

Spinelli

2008

COC

View full text Add to dashboard Cite

show abstract

“…The extent of this side reaction can be reduced by carrying out this reaction in a more dilute solution than is normally used (see Basic Protocol 2), although it also depends on the nucleopeptide-the longer the oligonucleotide chain, the higher the amount of acrylonitrile present in the reaction mixture and the higher the risk of alkylation. However, addition of cysteine hydrochloride to the deprotecting mixture has been shown to be very effective in scavenging acrylonitrile (Marchán et al, 2006).…”

Section: Deprotect Cysteine-containing Nucleopeptidementioning

confidence: 99%

“…Under the recommended conditions (aqueous methylamine, and [DTT+Cys]/nucleopeptide molar ratio ∼60), the level of alkylation of nucleopeptide Ac-Cys-Gly-Orn-Hse(p 3 dGCCATATGGC)-Ala-OH was negligible. Moreover, this treatment minimizes peptide degradation and allows isolation of cysteine-containing nucleopeptides in reasonable yields (Marchán et al, 2006).…”

Section: Deprotect Cysteine-containing Nucleopeptidementioning

confidence: 99%

Stepwise Solid‐Phase Synthesis of Nucleopeptides

Grandas

Marchán

Debéthune

et al. 2007

CP Nucleic Acid Chemistry

Self Cite

View full text Add to dashboard Cite

Phosphodiester-linked peptide-oligonucleotide conjugates (nucleopeptides) are obtained by stepwise solid-phase procedures. The peptide is first assembled on a suitably derivatized solid matrix and the oligonucleotide is subsequently elongated at the free hydroxyl group of the linking amino acid. Temporary acid-labile and permanent base-labile protecting groups are combined. Careful choice of the protection scheme is required to prevent and minimize side reactions that may degrade the target molecule.

show abstract

“…4.32.4). Once conjugation has been carried out according to Basic Protocol 4, the thiol group is deprotected by reaction with an excess of tris(n-butyl)phosphane at room temperature (Marchán et al, 2006b). Analysis, purification, and characterization are conducted as described in Basic Protocol 4.…”

Section: Preparation Of Cysteine-containing Peptide-oligonucleotide C...mentioning

confidence: 99%

Synthesis of Peptide‐Oligonucleotide Conjugates by Diels‐Alder Cycloaddition in Water

Marchán

Grandas

2007

CP Nucleic Acid Chemistry

Self Cite

View full text Add to dashboard Cite

Peptide-oligonucleotide conjugates incorporating all the nucleobases and trifunctional amino acids are obtained by Diels-Alder reaction between diene-modified oligonucleotides (2'-deoxyribo- or ribo-) and malemide-derivatized peptides. Both reagents are easily synthesized by on-column derivatization of the corresponding peptides and oligonucleotides. The cycloaddition reaction is carried out under mild conditions, in aqueous solution at 37 degrees C, affording the desired peptide-oligonucleotide conjugate with high purity and yield. The speed of the reaction depends on the size and composition of both reagents, but it is accelerated by the presence of positively charged amino acids in the peptide fragment. However, a small excess of maleimide-derivatized peptide may be required in some cases to complete the reaction within 8 to 10 hr.

show abstract

Linking the 3′ Ends of Oligonucleotide Duplexes with Cystine Disulfide Bridges

Cited by 5 publications

References 17 publications

Chemical Strategies for Oligonucleotide-Conjugates Synthesis

Chemical Strategies for Oligonucleotide-Conjugates Synthesis

Stepwise Solid‐Phase Synthesis of Nucleopeptides

Synthesis of Peptide‐Oligonucleotide Conjugates by Diels‐Alder Cycloaddition in Water

Contact Info

Product

Resources

About