3-azidopropanoate-N-hydroxysuccinimide ester

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3-azidopropanoate-N-hydroxysuccinimide ester

3-azidopropanoate-N-hydroxysuccinimide ester | 850180-76-6

Catalog Number R14-0324
Category Azides
Molecular Formula C7H8N4O4
Molecular Weight 212.16
Catalog Number Size Price Quantity

Product Introduction

3-azidopropanoate-N-hydroxysuccinimide ester is a small molecule reagent. As a versatile reactive reagent, it has a significant impact on bioconjugation and cross-linking applications. It is deeply embedded in the synthetic mechanism of drug delivery systems, effectively achieving precise targeted release of therapeutic drugs.

Chemical Information

Synonyms 3-Azidopropanoic acid NHS ester;Propanoic acid, 3-​azido-​, 2,​5-​dioxo-​1-​pyrrolidinyl ester ;
Purity ≥98%
IUPAC Name (2,5-dioxopyrrolidin-1-yl) 3-azidopropanoate
Canonical SMILES C1CC(=O)N(C1=O)OC(=O)CCN=[N+]=[N-]
InChI InChI=1S/C7H8N4O4/c8-10-9-4-3-7(14)15-11-5(12)1-2-6(11)13/h1-4H2
InChI Key WATICTZQAVLEKN-UHFFFAOYSA-N
Solubility DMSO, DCM, DMF
Appearance Soild powder
  • Product Specification
  • Application
Storage -20 °C

3-Azidopropanoate-N-hydroxysuccinimide ester, a versatile chemical reagent commonly utilized in bioconjugation and chemical biology, plays a pivotal role in diverse applications. Here are four key applications:

Protein Labeling: This ester finds frequent use in the labeling of proteins with fluorescent tags or other molecular probes, enabling precise site-specific modifications by reacting with amine groups. Such modifications are essential for visualizing protein localization, interactions, and dynamics in a myriad of biological studies, shedding light on the intricate details of cellular processes.

Click Chemistry: Serving as a crucial precursor in click chemistry reactions, 3-azidopropanoate-N-hydroxysuccinimide ester drives bioconjugation by efficiently clicking with alkynes to form stable triazole linkages. This mechanism underpins rapid and selective coupling of biomolecules in drug discovery and diagnostics, offering a powerful tool for streamlining research in the biomedical field.

Peptide Synthesis: In the realm of peptide synthesis, this ester facilitates the introduction of azide groups into peptide sequences, enabling subsequent modifications such as cyclization or attachment of bioactive moieties via click chemistry. These tailored modifications are indispensable for the development of peptide-based therapeutics and in-depth exploration of intricate protein-protein interactions, paving the way for groundbreaking advancements in biomedicine.

Molecular Probes Development: Beyond its core applications, this compound plays a vital role in crafting novel molecular probes for imaging and detection purposes through its azide functionality. This feature allows for versatile conjugation strategies with diverse reporter groups, enabling the creation of sensitive diagnostic tools and elevating the capabilities of bioanalytical assays to new heights, fueling advancements in medical diagnostics and research.

Computed Properties

XLogP3 0.1
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 6
Rotatable Bond Count 5
Exact Mass 212.05455475 g/mol
Monoisotopic Mass 212.05455475 g/mol
Topological Polar Surface Area 78Ų
Heavy Atom Count 15
Formal Charge 0
Complexity 331
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Patents

Publication NumberTitlePriority Date
WO-2020086311-A1 Thiophosphorodichloridate reagents for chemoselective histidine bioconjugation 2018-10-23
US-2021230215-A1 Thiophosphorodichloridate Reagents for Chemoselective Histidine Bioconjugation 2018-10-23
US-2016272669-A1 Novel reagents for universal site-specific labeling and modifications of nucleic acids 2015-03-17
US-9856285-B2 Reagents for universal site-specific labeling and modifications of nucleic acids 2015-03-17
US-10557853-B2 Molecular sensor and methods of use thereof 2012-12-31
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