Facile preparation of DNA-tagged carbohydrates

Sando, Shinsuke; Matsui, Kazuki; Niinomi, Yusuke; Sato, Naomi; Aoyama, Yasuhiro

doi:10.1016/s0960-894x(03)00559-6

Cited by 12 publications

(6 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Herein, we describe the use of quadruplexes to generate versatile supramolecular assemblies that orient, in a well‐defined manner, four organic fragments on one end of a parallel quadruplex for protein recognition. An earlier, although nonfunctional example of a functionalized tetraplex was demonstrated by Aoyama and co‐workers 14…”

Section: Methodsmentioning

confidence: 95%

Protein Recognition and Denaturation by Self‐Assembling Fragments on a DNA Quadruplex Scaffold

et al. 2006

View full text Add to dashboard Cite

show abstract

Section: Methodsmentioning

confidence: 95%

Protein Recognition and Denaturation by Self‐Assembling Fragments on a DNA Quadruplex Scaffold

et al. 2006

View full text Add to dashboard Cite

show abstract

“…Other simpler G-quadruplex forming oligonucleotides like Tetrahymena telomere dTG 4 T, which is able to self-assemble to give parallel tetramolecular structures, have been used as a G-quadruplex model in many applications involving binding processes and the identification of new ligands for anticancer therapy [25]. Interestingly, modifications of this G-quadruplex have also been reported by introducing carbohydrates [26] and cationic amino acids [27] using covalent strategies or the formation of supramolecular dendrimers. The use of [d(TG 4 T)] 4 quadruplex as a nanostructure to transport biomolecules has been scarcely investigated [27].…”

Section: Introductionmentioning

confidence: 99%

Tuning G-Quadruplex Nanostructures with Lipids. Towards Designing Hybrid Scaffolds for Oligonucleotide Delivery

Grijalvo

Eres

Gargallo

et al. 2020

IJMS

View full text Add to dashboard Cite

Two G-quadruplex forming oligonucleotides [d(TG4T)4 and d(TG6T)4] were selected as two tetramolecular quadruplex nanostructures because of their demonstrated ability to be modified with hydrophobic molecules. This allowed us to synthesize two series of G-quadruplex conjugates that differed in the number of G-tetrads, as well as in the terminal position of the lipid modification. Both solution and solid-phase syntheses were carried out to yield the corresponding lipid oligonucleotide conjugates modified at their 3′- and 5′-termini, respectively. Biophysical studies confirmed that the presence of saturated alkyl chains with different lengths did not affect the G-quadruplex integrity, but increased the stability. Next, the G-quadruplex domain was added to an 18-mer antisense oligonucleotide. Gene silencing studies confirmed the ability of such G-rich oligonucleotides to facilitate the inhibition of target Renilla luciferase without showing signs of toxicity in tumor cell lines.

show abstract

“…For these purposes, noncovalent carriers and covalent conjugates have been prepared. The methods described include electrostatic complexation of an oligonucleotide with glycosylated polylysine; chemical ligation to galactosylated polylysine, to a cholane scaffold, and to a neoglycopeptide; on-support glycosylation with trichloroacetimidates or unprotected carbohydrates; and the use of base moiety glycosylated nucleoside phosphoramidites and glycoside phosphoramidites as building blocks for the chain assembly. Some recent approaches allow creation of structural diversity in the terms of the number of sugar ligands and the distance between them.…”

Section: Introductionmentioning

confidence: 99%

Solid-Phase Synthesis of Oligonucleotide Glycoconjugates Bearing Three Different Glycosyl Groups: Orthogonally Protected Bis(hydroxymethyl)-N,N‘-bis(3-hydroxypropyl)malondiamide Phosphoramidite as Key Building Block

2004

View full text Add to dashboard Cite

Diethyl O,O'-(methoxymethylene)bis(hydroxymethyl)malonate (3) was observed to undergo a stepwise aminolysis when treated with 3-aminopropanol. This allowed convenient preparation of bis(hydroxymethyl)-N,N'-bis(3-hydroxypropyl)malondiamide bearing orthogonal levulinyl (Lev) and tert-butyldiphenylsilyl (TBDPS) protections at the two N-hydroxypropyl groups (8). One of the hydroxylmethyl functions was then protected with a 4,4'-dimethoxytrityl (DMTr) group, and the other one was phosphitylated to obtain a methyl N,N-diisopropylphosphoramidite (1). This building block was used for the synthesis of oligonucleotide glycoconjugates (25 and 26) carrying three different sugar units. After conventional phosphoramidite chain assembly of the sequence containing 1, the 5'-terminal DMTr group was removed and an appropriate glycosyl 6-O-phosphoramidite was coupled. The remaining protections of the branching unit were removed in the order of Lev and TBDPS, and the exposed hydroxyl functions were reacted one after another with the desired glycosyl 6-O-phosphoramidites. Global deprotection and cleavage of the conjugate from the support were achieved by conventional ammonolysis.

show abstract

Facile preparation of DNA-tagged carbohydrates

Cited by 12 publications

References 41 publications

Protein Recognition and Denaturation by Self‐Assembling Fragments on a DNA Quadruplex Scaffold

Protein Recognition and Denaturation by Self‐Assembling Fragments on a DNA Quadruplex Scaffold

Tuning G-Quadruplex Nanostructures with Lipids. Towards Designing Hybrid Scaffolds for Oligonucleotide Delivery

Solid-Phase Synthesis of Oligonucleotide Glycoconjugates Bearing Three Different Glycosyl Groups: Orthogonally Protected Bis(hydroxymethyl)-N,N‘-bis(3-hydroxypropyl)malondiamide Phosphoramidite as Key Building Block

Contact Info

Product

Resources

About