5-hexynoic NHS ester

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5-hexynoic NHS ester

5-hexynoic NHS ester | 906564-59-8

Catalog Number R01-0002
Category NHS Esters
Molecular Formula C10H11NO4
Molecular Weight 209.20
Catalog Number Size Price Quantity
R01-0002 -- $--

Chemical Information

Synonyms Alkyne NHS ester (hexynoic acid NHS ester);1-(5-Hexynoyloxy)-2,5-pyrrolidinedione;
Purity ≥98%
Canonical SMILES C#CCCCC(=O)ON1C(=O)CCC1=O
InChI InChI=1S/C10H11NO4/c1-2-3-4-5-10(14)15-11-8(12)6-7-9(11)13/h1H,3-7H2
InChI Key CXSSWEBEHUYETJ-UHFFFAOYSA-N
Solubility good in organic solvents (DMF, DMSO, DCM)
Appearance Soild powder
  • Application

5-hexynoic NHS ester is a versatile chemical reagent used in various biochemical and biotechnological applications. Here are some key applications of 5-hexynoic NHS ester:

Bioconjugation: 5-hexynoic NHS ester is widely used for bioconjugation reactions, where it facilitates the covalent attachment of biomolecules, such as proteins and peptides, to solid supports or other biomolecules. By reacting with amine groups, it forms stable amide bonds, enabling the creation of complex biomolecular assemblies. This is crucial for developing targeted drug delivery systems and diagnostic assays.

Click Chemistry: In the realm of click chemistry, 5-hexynoic NHS ester is employed as a component in azide-alkyne cycloaddition reactions. This enables the efficient and selective labeling of biomolecules with fluorescent tags or other probes for imaging and detection purposes. It provides a robust and reliable means of studying dynamic biological processes in vitro and in vivo.

Surface Functionalization: 5-hexynoic NHS ester can be used to functionalize surfaces of nanoparticles, microarrays, and biosensors with specific biomolecules. By modifying surfaces with 5-hexynoic NHS ester, researchers can immobilize enzymes, antibodies, or other ligands, creating highly specific and sensitive detection platforms. This application is crucial for developing advanced diagnostic tools and biosensors.

Protein Engineering: In protein engineering, 5-hexynoic NHS ester is utilized to introduce reactive handles for site-specific modifications of proteins. By selectively labeling proteins with 5-hexynoic NHS ester, researchers can introduce unique functional groups that enable further modifications, such as PEGylation or conjugation to therapeutic agents. This technology enhances protein stability, solubility, and therapeutic efficacy.

Computed Properties

XLogP3 0.1
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 5
Exact Mass 209.06880783 g/mol
Monoisotopic Mass 209.06880783 g/mol
Topological Polar Surface Area 63.7Ų
Heavy Atom Count 15
Formal Charge 0
Complexity 323
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-2022056273-A1 Lipid conjugates for the delivery of therapeutic agents 2020-09-11
EP-3889155-A1 Biomimetic g-quartet compounds 2020-03-31
WO-2021198239-A1 Biomimetic g-quartet compounds 2020-03-31
WO-2019242691-A1 Paclitaxel-lipid-polysaccharide dual-type conjugate, preparation method therefor and use thereof 2018-06-20
EP-3812376-A1 Paclitaxel-lipid-polysaccharide dual-type conjugate, preparation method therefor and use thereof 2018-06-20
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