D-Ristosamine CAS No. 62774-43-0

Product Description

D-Ristosamine is a deoxyamino sugar derivative, structurally characterized as a 3-amino-2,3,6-trideoxy-D-arabino-hexose. It is a key component in glycosidic antibiotics such as ristocetin and ristomycin, contributing to their antibiotic binding specificity, biological activity, and water solubility. Functionally, it features a primary amine (-NH₂) group, hydroxyl (-OH) groups, and a hexose backbone. Structurally, it is derived from D-ribose by removing oxygen atoms at positions 2, 3, and 6, and adding an amino group at position 3. D-Ristosamine can be synthesized from simpler sugars like D-glucose or D-mannose through deoxygenation, amination, and stereochemical control. Its enantiomer, L-Ristosamine, is found in ristomycins, which are part of the vancomycin family of antibiotics. While its direct applications are limited, its structural similarity to other biologically active amino sugars suggests potential in medicinal chemistry research, particularly in developing new antimicrobial or anticancer drugs.

Product Use & Characteristics

Molecular Formula: C₆H₁₃NO₃
Molecular Weight: 147.17 g/mol
IUPAC Name: (3S,4S,5R)-3-amino-4,5-dihydroxyhexanal
Structure: D-Ristosamine is a trideoxyhexose derivative with a pyranose ring (a six-membered ring containing five carbon atoms and one oxygen atom). It is characterized by a primary amine (-NH₂) group, hydroxyl (-OH) groups, and a hexose backbone (6-carbon sugar). The "ribo" configuration indicates the specific arrangement of hydroxyl groups and the amino group around the sugar ring, relative to the reference sugar D-ribose.
Isomer: D-Ristosamine is the C-5 epimer of D-daunosamine. Its L-isomer, L-ristosamine, is a component of the antibiotic ristomycin.
Configuration: D-series sugar with specific stereochemistry (2,6-dideoxy, 3-amino). It is structurally related to other deoxy amino sugars like D-daunosamine and D-vancosamine.

Synthesis Methods

D-Ristosamine and its derivatives can be synthesized through various chemical routes, often starting from other carbohydrate precursors like D-glucose or L-rhamnose, or even non-carbohydrate materials using asymmetric aldol strategies. Synthetic approaches often involve protecting group strategies to achieve the correct stereochemistry for the amino and hydroxyl groups.

• Starting Materials: Commonly derived from simpler sugars such as D-glucose or D-mannose.

• Key Steps: Deoxygenation, amination, and stereochemical control.

• Protecting Group Strategies: Often used to achieve the correct configuration.

Uses

Antibiotics: D-Ristosamine is a component of glycosidic antibiotics such as ristocetin and ristomycin, which are glycopeptide antibiotics.

• Binding Specificity: Contributes to antibiotic binding specificity.

• Biological Activity: Modulates the biological activity of the parent antibiotic.

• Water Solubility and Transport: Enhances water solubility and transport properties of the antibiotic.

Medicinal Chemistry

• Drug Development: Its structural similarity to other biologically active amino sugars (like L-daunosamine, found in anthracycline antitumor antibiotics) suggests its potential in the development of new drugs with antimicrobial or anticancer properties.

• Natural Products: Amino sugars like D-Ristosamine are crucial components of many natural products, including antibiotics and anticancer agents. They can form glycosidic bonds in complex carbohydrates, which are essential for cell signaling, immune response, and other biological processes.

Antiviral Activity: Derivatives of ristosamine, such as L-Ristosamine nucleoside, have shown antiviral activity (e.g., against HIV and HSV-1).

Related Compounds

• L-Ristosamine: The enantiomer, found in some natural products.

• D-Vancosamine: A similar sugar found in vancomycin.

• D-Daunosamine: Present in the anticancer drug daunorubicin.

Biological Significance

• Antibiotic Role: Found as a glycosidic moiety in ristocetin A, an antibiotic historically used against Gram-positive bacteria (though withdrawn due to toxicity). It plays a role in the binding and activity of the parent antibiotic, influencing its interaction with bacterial cell wall precursors (e.g., binding to D-Ala-D-Ala termini in peptidoglycan).

• Medical Diagnosis: L-Ristosamine, the enantiomer of D-Ristosamine, is a component of ristomycins, which are used in diagnosing certain variants of von Willebrand disease due to their ability to cause platelet aggregation.

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