Acarbose

Cat. No.: B1140619

CAS No.: 56810-94-0

M. Wt: 645.6

InChI Key:

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Overview

1. Description

5. Mechanism of action

2. Preparation methods

6. Comparison with similar compounds

3. Chemical reactions analysis

7. Properties

4. Scientific research applications

8. Disclaimer

Description

Acarbose is a complex oligosaccharide that acts as an inhibitor of several enzymes responsible for the breakdown of complex carbohydrates in the intestines. It is primarily used as an anti-diabetic drug to manage type 2 diabetes mellitus by controlling postprandial blood glucose levels. This compound works by inhibiting alpha-glucosidase, an intestinal enzyme that releases glucose from larger carbohydrates such as starch and sucrose .

Preparation Methods

Synthetic Routes and Reaction Conditions: Acarbose is produced through a fermentation process involving the bacterium Actinoplanes sp. The biosynthesis involves the formation of acarviosin, which is then linked to maltose. The fermentation process is optimized by controlling the osmolality of the fermentation solution, which significantly affects the yield of this compound .

Industrial Production Methods: Industrial production of this compound involves large-scale fermentation using optimized conditions to maximize yield. The process includes the use of specific carbon sources, such as a mixture of maltose and glucose, to enhance the biosynthesis of this compound. The fermentation is carried out in bioreactors with controlled parameters such as temperature, pH, and oxygen supply .

Chemical Reactions Analysis

Types of Reactions: Acarbose undergoes various chemical reactions, including hydrolysis and enzymatic degradation. It is primarily involved in inhibition reactions where it binds to alpha-glucosidase enzymes, preventing the breakdown of complex carbohydrates .

Common Reagents and Conditions: The common reagents used in the reactions involving this compound include alpha-glucosidase enzymes and substrates such as maltose and sucrose. The reactions typically occur under physiological conditions in the gastrointestinal tract .

Major Products Formed: The major products formed from the reactions involving this compound are glucose and other simple sugars, which are released from the breakdown of complex carbohydrates .

Scientific Research Applications

Acarbose has a wide range of scientific research applications, including:

Chemistry: this compound is used as a model compound to study enzyme inhibition and carbohydrate metabolism.

Biology: It is used to investigate the role of alpha-glucosidase in various biological processes and to study the effects of enzyme inhibition on cellular functions.

Medicine: this compound is widely used in the treatment of type 2 diabetes mellitus to control postprandial blood glucose levels. .

Industry: this compound is used in the pharmaceutical industry for the production of anti-diabetic medications. .

Mechanism of Action

Acarbose exerts its effects by inhibiting alpha-glucosidase enzymes located in the brush-border of the intestinal mucosa. These enzymes are responsible for metabolizing oligo-, tri-, and disaccharides into absorbable simple sugars. By inhibiting these enzymes, this compound limits the absorption of dietary carbohydrates and reduces the postprandial increase in blood glucose and insulin levels . The inhibition is competitive and reversible, and this compound mimics the transition state of the substrate with its amine linkage .

Comparison with Similar Compounds

Voglibose: Another alpha-glucosidase inhibitor used to manage postprandial blood glucose levels in diabetic patients.

Miglitol: An alpha-glucosidase inhibitor that is structurally different from acarbose and voglibose.

Uniqueness of this compound: this compound is unique due to its complex oligosaccharide structure and its ability to inhibit multiple enzymes involved in carbohydrate metabolism. It has been shown to be effective in reducing postprandial blood glucose levels and improving cardiovascular outcomes in diabetic patients .

Properties

	{ "Design of the Synthesis Pathway": "The synthesis pathway of Acarbose involves the coupling of a pseudotrisaccharide with a glucose derivative. The pseudotrisaccharide is synthesized from a disaccharide and a monosaccharide. The glucose derivative is obtained from a glucose molecule through a series of reactions. The two compounds are then coupled together to form Acarbose.", "Starting Materials": [ "Sucrose", "Glucose", "Phenylhydrazine", "Sodium nitrite", "Sodium borohydride", "Acetic anhydride", "Acetone", "Hydrochloric acid", "Sodium hydroxide", "Methanol", "Ethanol", "Chloroacetyl chloride", "Triethylamine", "Sodium methoxide", "Methyl iodide", "Ethyl iodide", "Benzyl bromide", "Sodium cyanoborohydride", "Sodium hydride", "Tetrahydrofuran", "Dimethylformamide", "Dimethyl sulfoxide", "Methanesulfonic acid", "Sodium azide", "Sodium periodate", "Sodium bisulfite", "Sodium chloride", "Water" ], "Reaction": [ "Sucrose is reacted with phenylhydrazine and sodium nitrite to form a pseudotrisaccharide intermediate.", "The pseudotrisaccharide intermediate is reduced with sodium borohydride to form the corresponding alcohol.", "The alcohol is acetylated with acetic anhydride and acetic acid to form the corresponding acetate.", "The acetate is treated with sodium hydroxide to form the corresponding glucose derivative.", "Glucose is reacted with chloroacetyl chloride and triethylamine to form the corresponding chloroacetate.", "The chloroacetate is treated with sodium methoxide to form the corresponding methyl ether.", "The methyl ether is reacted with methyl iodide or ethyl iodide to form the corresponding iodide.", "The iodide is reacted with benzyl bromide to form the corresponding benzyl ether.", "The benzyl ether is reduced with sodium cyanoborohydride to form the corresponding alcohol.", "The alcohol is treated with sodium hydride and tetrahydrofuran to form the corresponding alkoxide.", "The alkoxide is reacted with the glucose derivative to form Acarbose.", "The Acarbose is purified using various techniques such as column chromatography, recrystallization, and HPLC." ] }
CAS No.	56810-94-0
Molecular Formula	C25H43NO18
Molecular Weight	645.6
Origin of Product	United States

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