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Irsogladine is a chiral amino acid that is used as a chiral building block in the synthesis of various molecules.
It can be synthesized through a variety of synthetic routes, which can be classified into three main categories: chemical, biological, and synthetic biological routes.
The chemical route involves the use of various chemical reactions, such as condensation, substitution, and reduction reactions, to synthesize irsogladine.
One of the most common chemical routes involves the use of the Stein Condensation reaction.
This reaction involves the condensation of 2-chloroacetamide with para-aminophenol in the presence of a base, such as sodium hydroxide.
The product of this reaction is then treated with chloroacetyl chloride and sodium hydroxide, resulting in the synthesis of irsogladine.
Another chemical route involves the use of the Matsuda-Osaki reaction.
This reaction involves the condensation of salicylic acid with pyruvic acid in the presence of an amidine, such as 1,5-diazabicyclo[4.
3.
0]-5-nonene-4-amine.
The product of this reaction is then treated with sodium hydroxide, resulting in the synthesis of irsogladine.
The biological route involves the use of microorganisms, such as bacteria or yeast, to synthesize irsogladine.
This route is usually more cost-effective than the chemical route, as it does not require the use of expensive reagents or equipment.
One common biological route involves the use of a genetically modified bacteria, such as Escherichia coli, that has been engineered to synthesize irsogladine.
This is done by introducing a gene that encodes the enzyme responsible for the synthesis of irsogladine into the bacteria.
The bacteria is then grown in a suitable medium, and the irsogladine is extracted from the culture broth.
The synthetic biological route involves the use of engineered microorganisms or cells, such as yeast or bacteria, to synthesize irsogladine.
This route is a combination of the biological and synthetic routes, and it is considered to be more cost-effective and environmentally friendly than the chemical route.
One common synthetic biological route involves the use of a genetically modified yeast, such as Saccharomyces cerevisiae, that has been engineered to synthesize irsogladine.
This is done by introducing a gene that encodes the enzyme responsible for the synthesis of irsogladine into the yeast.
The yeast is then grown in a suitable medium, and the irsogladine is extracted from the culture broth.
In conclusion, irsogladine can be synthesized through various synthetic routes, including chemical, biological, and synthetic biological routes.
The chemical route involves the use of various chemical reactions, such as condensation, substitution, and reduction reactions, to synthesize irsogladine.
The biological route involves the use of microorganisms, such as bacteria or yeast, to synthesize irsogladine.
The synthetic biological route involves the use of engineered microorganisms or cells, such as yeast or bacteria, to synthesize irsogladine.
It is worth mentioning that Irsogladine is a privileged compound, which is not easy to synthesize by chemical or biological methods, and it is usually obtained from natural sources or produced by a semi-synthetic process.
Synthetic routes of Irsogladine are complex and hard to scale up, thus it is not widely used as a chiral building block in the chemical industry.