CAS: 1635433-54-3—New probe for metabolic regulation research

2-[(1-Pentynoyl)amino]-2-deoxy-D-glucose is an innovative molecule in the field of metabolic probe reagents, providing a powerful tool for revealing metabolic networks and regulatory mechanisms in living bodies. As a structural analog of glucose, this compound combines the ability to participate in sugar metabolism with click chemistry compatibility through clever chemical modifications, making it a key reagent in cell metabolism research, disease mechanism exploration, and drug development. In cutting-edge research on metabolic diseases such as diabetes, cancer, and immunometabolism, such molecules are gradually showing indispensable value, helping scientists decipher the complex mysteries of energy balance, signal transduction, and biosynthetic pathways.

Chemical Information

Chemical name: 2-[(1-pentynoyl)amino]-2-deoxy-D-glucose

Common name: 2-deoxy-2-[(1-oxo-4-pentyn-1-yl)amino]-beta-D-glucose

Chemical formula: C11H17NO6

Molecular weight: 259.26 g/mol

CAS number: 1635433-54-3

Category: Metabolic Probe Reagents

Structural features

The structural design of 2-[(1-pentynoyl)amino]-2-deoxy-D-glucose embodies the concept of precision molecular engineering. Its unique feature lies in the double modification of the natural glucose skeleton, thereby giving it excellent functionality.

Basics of sugar ring modification: This molecule uses D-glucose as a template, deoxygenates the carbon atom at position 2 and introduces amino substitution. This change eliminates the polarity of the 2-hydroxyl group of natural glucose and at the same time enhances the interaction potential between the molecule and enzymes or receptors in biological systems through the amino linkage. It may affect the recognition of sugar transporters or the activity of metabolic enzymes, laying the foundation for simulating or interfering with natural sugar metabolism pathways.

Integration of alkynyl functional groups: The amino group is further combined with the 1-pentynoyl group to form an amide bond. The alkyne bond (-C≡CH) at the end of the pentynyl chain is a highly reactive functional group that provides an ideal platform for click chemistry applications. This alkyne bond structure allows specific covalent attachment to azide labels such as fluorescent dyes, biotin, or affinity tags via a copper-catalyzed azide-alkyne cycloaddition reaction under mild conditions. This modular labeling strategy not only achieves highly sensitive detection but also avoids interfering with the normal metabolic processes of cells.

Stability and osmotic balance: The stability of C-C glycosidic bonds and amide bonds ensures the persistence of the molecule in physiological environments, while the introduction of hydrophobic alkyne chains may optimize lipid solubility and promote cell membrane penetration. The overall structure balances metabolic involvement and chemical reporting capabilities, allowing it to serve as a "Trojan horse" probe to release signals within cells or capture metabolic intermediates.

This structural combination enables 2-[(1-pentynyl)amino]-2-deoxy-D-glucose to surpass traditional glucose analogs and become a multifunctional metabolic probe that can be integrated into glycolysis, hexosamine or glycogen synthesis pathways, and can achieve spatiotemporally resolved labeling and tracking through acetylenic bonds.

Main applications and advantages

Dynamic visualization and quantitative analysis of metabolic pathways

As a glucose analog, this compound can be recognized and internalized by cellular glucose transporters, and subsequently participates in or competitively inhibits core metabolic pathways. The alkyne bond labeling capability enables dynamic imaging of sugar uptake, glycolytic flux, or mitochondrial metabolism in living cells or tissue samples via click chemistry combined with fluorescent probes. For example, in cancer research, tumor cells often rely on glycolysis for energy, and this probe can be used to visualize the metabolic reprogramming of cancer cells in real time; in immune cell research, it can analyze changes in energy requirements in the activated state. This tracking advantage of high spatial and temporal resolution makes up for the limitations of traditional isotope labeling or antibody detection, providing a safer and more flexible tool for metabolic flux analysis.

Analysis of protein glycosylation modification mechanism

2-Deoxyglucose derivatives are often used as chemical probes or inhibitors of the O-GlcNAc glycosylation pathway. This compound may affect the O-GlcNAc modification level of proteins by incorporating into the intracellular UDP-GlcNAc pool. This post-translational modification regulates key processes such as transcription, signal transduction and cell cycle. The presence of alkyne bonds allows modified proteins to be enriched and identified by mass spectrometry through click chemistry, thereby mapping O-GlcNAc modifications on a large scale and revealing its role in metabolic diseases, neurodegenerative diseases or developmental abnormalities. This application expands the depth of glycobiology research and helps discover new biomarkers or drug targets.

Metabolic disease model construction and drug screening platform

This probe can be used to construct in vitro or in vivo metabolic reporter systems in studies of diabetes, obesity, or rare metabolic disorders. Assess changes in glucose metabolism under insulin resistance, lipid accumulation, or mitochondrial dysfunction by labeling cells or animal models. In addition, it is compatible with high-throughput screening processes and can be used as a readout tool to test the metabolic modulating effects of small molecule compounds or biologics, accelerating drug development targeting metabolic enzymes or transporters. This advantage reduces the risk of false positives in early development and improves target specificity.

Exploration of basic metabolic regulation network

Beyond applications, this compound provides basic science with a window into metabolic regulatory networks. For example, combined with genome editing or single-cell technologies, the role of metabolic heterogeneity in stem cell differentiation, aging, or response to infection can be dissected. The chemical orthogonality of alkyne bonds also allows multimodal detection, such as simultaneous fluorescence imaging and electron microscopy, to localize metabolic activity at the suborganelle level. These functions drive systems biology and promote an integrated understanding of energy homeostasis, oxidative stress, and anabolism.

Conclusion

2-[(1-Pentynoyl)amino]-2-deoxy-D-glucose is not just a simple sugar derivative, it is a bridge molecule connecting chemical synthesis and life metabolism. From decoding cellular energy codes to developing precision metabolic therapies, its potential is being unleashed as chemical biology advances advance. As personalized medicine and metabolic health receive increasing attention today, this type of probe reagents will continue to empower cutting-edge research and contribute key insights to human understanding of the nature of diseases and innovative treatment strategies.

The above information is provided by the editor of KASONS and is for scientific research only.