153248-52-3

Basic information

• Product Name: 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid
• Synonyms: 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid;a-NeuraMinic acid, N-acetyl-2-O-(5-broMo-4-chloro-1H-indol-3-yl)-;(2S,4S,5R,6R)-5-Acetamido-2-((5-bromo-4-chloro-1H-indol-3-yl)oxy)-4-hydroxy-6-((1R,2R)-1,2,3-t;5-bromo-4-chloro-indol-3-yl-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)
• CAS NO: 153248-52-3
• Molecular Formula: C19H22BrClN2O9
• Molecular Weight: 537.74298
• Mol File: 153248-52-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid(153248-52-3)
• EPA Substance Registry System: 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid(153248-52-3)

Safety Data

• Hazardous Substances Data: 153248-52-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-O-(5-broMo-4-chloroindol-3-yl)sialic acid is utilized as a research compound for its potential to interact with proteins and other molecules, which is crucial in the fields of glycobiology and glycochemistry. Its unique structure allows it to be a valuable tool in studying the roles of sialic acid in biological systems and its interactions with various biomolecules.
Used in Glycobiology:
In the field of glycobiology, 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid serves as a key molecule for understanding the complex carbohydrate structures on cell surfaces. Its presence can provide insights into cell recognition, signaling, and adhesion processes, which are vital for various biological functions.
Used in Glycochemistry:
2-O-(5-broMo-4-chloroindol-3-yl)sialic acid is employed as a glycochemical agent to explore the synthesis and modification of carbohydrate-containing compounds. Its unique functional groups can be harnessed to develop new glycoconjugates and glycoclusters, which may have applications in drug development and diagnostics.
Used in Drug Development:
2-O-(5-broMo-4-chloroindol-3-yl)sialic acid is used as a lead compound in drug development, particularly for targeting sialic acid-binding proteins. Its potential to modulate protein-carbohydrate interactions could lead to the discovery of new therapeutic agents for various diseases.
Used in Diagnostics:
In the diagnostics industry, 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid may be utilized as a biomarker or a component of diagnostic assays. Its specific binding properties could be leveraged to develop sensitive and selective tests for detecting diseases or monitoring treatment responses.

Upstream product

• 1447125-22-5 C₁₃H₉BrClNO₅ 
• 1447125-25-8 C₁₅H₁₅BrClNO₄ 
• 1447125-28-1 5-bromo-4-chloroindoxylic acid allyl ester 
• 1447125-42-9 5-bromo-4-chloro-indox-3-ylic acid allyl ester-(methyl-5-acetamido-4,7,8,9-tetra-Oacetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate) 
• 627531-47-9 4-amino-2-chloro-3-methylbromobenzene 
• 153248-53-4 (N-acetyl-5-bromo-4-chloro-indol-3-yl)-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate) 
• 1447125-47-4 (5-bromo-4-chloro-indol-3-yl)-(methyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate) 
• 125328-80-5 N-(4-bromo-3-chloro-2-methylphenyl)acetamide 
• 125328-77-0 N-acetyl-5-bromo-6-chloroanthranilic acid 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 7463-35-6 N-(3-chloro-2-methylphenyl)acetamide 
• 3030-19-1 2-amino-5-bromo-6-chlorobenzoic acid 
• 943138-45-2 5-bromo-6-chloro-isatoic anhydride 
• 2148-56-3 2-chloro-6-aminobenzoic acid 

Relevant articles and documents

Differences in reactivity of N-acetyl- and N,N-diacetylsialyl chlorides caused by their different supramolecular organization in solutions

O-Sialylation of a substituted indolin-3-one under phase-transfer catalysis conditions, which does not occur when N-acetylsialyl chloride is used, proceeds with N,N-diacetylsialyl chloride as the glycosyl donor. A study using dynamic light scattering of solutions of both sialyl chlorides under conditions close to the conditions used for glycosylation showed a difference in the correlation radii of light scattering particles in such solutions. This suggests that the introduction of an additional N-acetyl group into the sialyl chloride significantly alters the structure of the supramers of glycosyl donor, which apparently have an increased accessibility of individual molecules for the attack by a nucleophile, which increases its reactivity.

Synthesis method of 5-bromo-4-chloro-3-indolyl-alpha-D-N-acetylneuraminic acid sodium salt

The invention provides a synthesis method of 5-bromo-4-chloro-3-indolyl-alpha-D-N-acetylneuraminic acid sodium salt. In the prior art, a lot of inflammable and explosive compounds are used, methyl is oxidized through potassium permanganate to form acid, and the potassium permanganate is the explosive compound; triphosgene is used and dangers are easy to occur; sodium hydride is used and the compound is combusted when meeting water, and then is exploded; the requirements on operation are very high. In a process route of the prior art, a lot of waste acids are generated and influences on the environment are relatively great; noble metal including silver and palladium is used in the process so that reaction cost is high, and heavy metal remains in a product and influences on the quality of the product are very great. The invention provides a preparation method which is simple to operate, high in safety, few in side reactions, high in conversion rate, high in yield, small in environment pollution and low in production cost and is suitable for industrial production.

Novel efficient routes to indoxyl glycosides for monitoring glycosidase activities

A new efficient synthesis for broad access to indoxyl glycosides was developed. Indoxylic acid allyl ester linked to a sugar structure served as the key intermediate in this route. Selective ester cleavage and mild decarboxylation led to the corresponding indoxyl glycosides in good yields. This synthesis was applied for preparation of indoxyl glycosides of fucose, sialic acid, and 6′-sialyl lactose.