Ac4GalNAz,叠氮修饰半乳糖,

1,3,4,6-四-氧-乙酰基-2-[(叠氮乙酰基)氨基]-2-脱氧-β-D-吡喃半乳糖

1,3,4,6-Tetra-O-acetyl-N-azidoacetylgalactosamine is an azido-tagged analogue of N-acetylgalactosamine. It features azide functionality on the N-acyl side chain and is acetylated to aid in cell membrane permeation. It is metabolised by mammalian cells and incorporated into mucin-type-O-linked glycoproteins. The azide functionality is exploited as a biorthogonal functional group that can be reacted with phosphine probes by the Staudinger ligation.

Ac4GalNAz is a synthetic sugar analogue that can be used in the study of glycobiology. Glycobiology is the study of the structure and function of carbohydrates (glycans) in biological systems. Ac4GalNAz is a derivative of GalNAc (N-acetylgalactosamine) and contains an azide group (N3) which can be labeled with a fluorescent dye to detect glycan structures in living cells.

Definition and Background:

Ac4GalNAz is a synthetic sugar that can be used to label and identify glycans in biological systems. It was first introduced in 2005 by Carolyn Bertozzi and colleagues at the University of California, Berkeley. The compound has been used extensively to label and track glycan structures in various living systems.

Synthesis and Characterization:

Ac4GalNAz can be synthesized from commercially available starting materials using a few synthetic steps. The synthesis involves the acetylation of GalNAc followed by the addition of an azide group using a suitable azide reagent. The product is purified by chromatography and characterized by spectroscopic methods.

Analytical Methods:

Ac4GalNAz can be analyzed using various methods such as HPLC, LC-MS, and NMR spectroscopy. These methods can be used to determine the purity, identity, and quantity of the compound.

Biological Properties:

Ac4GalNAz can be incorporated into glycans in living cells through the action of endogenous glycosyltransferases. Once incorporated, the compound can be labeled with a fluorescent dye to detect and track glycan structures in living cells. Ac4GalNAz has been shown to be non-toxic to cells and does not affect cell viability.

Toxicity and Safety in Scientific Experiments:

Ac4GalNAz is generally considered safe to use in scientific experiments. However, it is important to use appropriate safety measures such as wearing gloves and lab coats, and handling the compound in a fume hood. The compound should also be stored and disposed of in accordance with local regulations.

Applications in Scientific Experiments:

Ac4GalNAz has been used in various experiments to study the role of glycan structures in biological systems. The compound has been used to label and track glycan structures in living cells, tissues, and organisms. It has been used in studies of bacterial and viral infections, as well as in studies of cancer and autoimmune diseases.

Current State of Research:

Research on Ac4GalNAz and its applications in glycobiology is ongoing. New methods and techniques are being developed to improve the labeling and detection of glycan structures using Ac4GalNAz. The compound is also being used in studies of glycosylation-related diseases and their treatments.

Potential Implications in Various Fields of Research and Industry:

Ac4GalNAz has potential implications in various fields of research and industry. In glycobiology, the compound can be used to study the role of glycan structures in disease development and treatment. In drug discovery, Ac4GalNAz can be used to screen for glycosylation-related targets and to develop glycan-based therapeutics. The compound can also be used in the food and agriculture industry to study glycan structures in plant cells and to develop new crop varieties.

Limitations and Future Directions:

Although Ac4GalNAz has many potential applications, there are also limitations to its use. These include the need for specific labeling and detection protocols, as well as the potential for interfering with endogenous glycan structures. Future research directions include the development of new labeling and detection methods, the study of glycan structures in different organisms and tissues, and the exploration of new applications in various fields.