Synthesis of Carbohydrate–Oligonucleotide Conjugates and Their Applications

Morales, Juan Carlos

doi:10.1002/9783527812103.ch10

Cited by 1 publication

(3 citation statements)

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“…The advantage of this reaction is its efficiency and orthogonality. For example, azide-modified hyaluronic acid and chondroitin sulfates with variable sulfate patterns have been synthesized and conjugated with cyclooctyne-modified oligonucleotides (Jadhav et al, 2016 and2018).…”

Section: Commentary Background Informationmentioning

confidence: 99%

“…Covalent hybrid molecules of oligonucleotides and carbohydrates have received marked interest for improving both diano‐ and pharmacophoric properties of oligonucleotide therapeutics (Benizri et al., 2019; Morales, 2018). The N ‐acetylgalactosamine (GalNAc) concept (Valentijn et al., 1997) is applied by Alnylam Pharmaceuticals to target siRNAs efficiently to hepatocytes.…”

Section: Commentarymentioning

confidence: 99%

“…For synthesis of oligonucleotide glycoconjugates, a diverse set of conjugation strategies is available (Morales, 2018). Appropriate phoshoramidite building blocks of sugars have been prepared and used as an integral part of automated assembly to produce both terminal and intrachain glycomodifications in an oligonucleotide sequence (Dubber & Fréchet, 2003; Granqvist, Kraszewski, Tähtinen, & Virta, 2017; Katajisto, Heinonen, & Lönnberg, 2004; Ketomäki & Virta, 2008).…”

Section: Commentarymentioning

confidence: 99%

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Immobilized Carbohydrates for Preparation of 3′‐Glycoconjugated Oligonucleotides

Österlund

Aho

Äärelä

et al. 2020

CP Nucleic Acid Chemistry

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A detailed protocol for preparation 3′‐glycoconjugated oligonucleotides is described based on one‐pot immobilization of 4,4′‐dimethoxytrityl‐protected carbohydrates to a solid support followed by on‐support peracetylation and automated oligonucleotide assembly. Compared to an appropriate building block approach and post‐synthetic manipulation of oligonucleotides, this protocol may simplify the synthesis scheme and increase overall yield of the conjugates. Furthermore, the immobilization to a solid support typically increases the stability of reactants, enabling prolonged storage, and makes subsequent processing convenient. Automated assembly on these carbohydrate‐modified supports using conventional phosphoramidite chemistry produces 3′‐glycoconjugated oligonucleotides in relatively high yield and purity. © 2020 Wiley Periodicals LLC. Basic Protocol 1: Synthesis of 1‐O‐tert‐butyldimethylsilyl‐6‐O‐(4,4′‐dimethoxytrityl)‐β‐D‐glucose Basic Protocol 2: Synthesis of 6‐O‐dimethoxytrityl‐2,3,1′,3′,4′,6′‐hexa‐O‐benzoylsucrose Basic Protocol 3: Synthesis of 6″‐O‐dimethoxytrityl‐N‐trifluoroacetyl‐protected aminoglycosides Basic Protocol 4: Synthesis of 3‐O‐dimethoxytrityl‐propyl β‐D‐galactopyranoside Basic Protocol 5: Synthesis of trivalent N‐acetyl galactosamine cluster Basic Protocol 6: Synthesis of carbohydrate monosuccinates and their immobilization to a solid support Basic Protocol 7: Oligonucleotide synthesis using immobilized carbohydrates

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Section: Commentary Background Informationmentioning

confidence: 99%