Alkynyl-based Ribose Modification Service
Professional Alkynyl-based Ribose Modification That Exceeding Your Expectations
Effective approaches to the modification of ribose and the extension of its function are important for conducting biomedical research and developing novel drugs. CD BioGlyco has always been committed to providing clients with professional GlycoCLICK™-based Modification Services. Over the past several decades, our capabilities have expanded globally, providing researchers with access to comprehensive alkynyl-based ribose modification support. Below are the comprehensive details of the outstanding services we provide:
- First, we select an appropriate starting material and protect the hydroxyl group on the starting material to selectively introduce the alkyne group. The alkyne functional group is then introduced by reacting the compound with an alkyne reagent, which we commonly use such as propargyl alcohol, alkyne bromide, or alkyne acid. Finally, the protecting group is removed to obtain the ribose precursor containing the alkyne group.
- Subsequently, we used azides and alkynyl compounds in organic reaction solvents and introduced copper catalysts to the reaction solution in appropriate amounts of a base (e.g., Na2CO3 or K2CO3) to facilitate the reaction. The reaction temperature and reaction time depend on the particular reactants and reaction conditions and usually vary from a few hours to a few days at room temperature.
- Finally, our experts use column chromatography (e.g., silica gel column chromatography, gel column chromatography, or reversed-phase column chromatography) to separate and purify the products. Suitable crystallization, washing, and drying steps are then employed to obtain pure target products.
Fig.1 Flowchart of alkynyl-based ribose modification. (CD BioGlyco)
Publication Data
Technology: Matrix-assisted laser desorption/ionization (MALDI) and electrospray ionization (ESI)
Journal: ACS Chemical Biology
IF: 4.634
Published: 2014
Results: This article focuses on the structure and reactivity of two motifs, 7-ethynyl-8-aza-7-deazaadenosine (7-EAA) and 7-triazolyl-8-aza-7-deazaadenosine (7-EAA-triazole), in RNA. Specifically, the researchers introduced these two modification groups in RNA molecules by copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and analyzed their structure and reactivity. They found that the two modification groups could exist stably in the RNA molecule and had no obvious effect on the structure and function of RNA. They concluded that the rate of CuAAC reaction is affected by the secondary structure of RNA and that single-stranded regions react faster than double-stranded regions. Finally, the researchers assessed the reactivity of RNA containing 7-EAA and 7-EAA-derived triazoles by reacting it with two different RNA processing enzymes (reverse transcriptase and adenylate deaminase). These experiments showed that reverse transcriptase recognized 7-EAA and 7-EAA-derived triazoles as adenosine on the template strand. In contrast, adenylate deaminase deaminates only 7-EAA-containing RNA and does not react with 7-EAA-derived triazoles.
Fig.1 Crystal structure of 7-ethynyl-8-aza-7-deazaadenosine-triazole modified RNA. (Phelps, et al., 2014)
Applications
- The alkynyl-based ribose modification is applied to the localization and visualization of RNAs by alkyne labeling of target RNAs in cells or tissues using click chemistry reactions to bind fluorescent dyes or other probes to them.
- By introducing alkyne labels to specific sites in the target RNA, affinity labels such as biotin are bound to them and thus applied to the research on the interaction of RNA with specific proteins.
- The introduction of alkyne groups on RNA molecules allows the design and synthesis of ligands with high selectivity and affinity for targeting specific non-coding RNAs, non-traditional mRNAs, or pathologically relevant RNA molecules.
Advantages
- It allows the targeted modification of RNA molecules without affecting the overall structure and function of RNA molecules.
- This technique is highly selective and sensitive and can be used to distinguish different bases and structures in RNA molecules for precise localization and detection of RNA molecules.
- We regulate the degree and location of modification by controlling parameters such as the concentration of modifiers and markers, reaction conditions, and time, thus realizing dynamic modification and regulation of RNA.
CD BioGlyco is a well-established company known for its extensive experience and exceptional reputation in offering alkynyl-based ribose modification services. With our highly skilled researchers, we are dedicated to facilitating a more comprehensive and accurate exploration of glycobiology. For further details, please don't hesitate to contact us.
Reference
- Phelps, K.J.; et al. Click modification of RNA at adenosine: structure and reactivity of 7-ethynyl-and 7-triazolyl-8-aza-7-deazaadenosine in RNA. ACS Chemical Biology. 2014, 9(8): 1780-1787.
For research use only. Not intended for any clinical use.
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