25055-86-1

Basic information

• Product Name: 3-(3-Methyl-3H-diazirine-3-yl)propionic acid
• Synonyms: 3-(3-Methyl-3H-diazirine-3-yl)propionic acid;3-Methyl-3H-diazirine-3-propionic acid;3-Methyl-diazirine-3-propanoic Acid;3-(3-methyl-3H-diazirin-3-yl)propanoic acid
• CAS NO: 25055-86-1
• Molecular Formula: C₅H₈N₂O₂
• Molecular Weight: 128.12922
• Mol File: 25055-86-1.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 233.0±32.0℃ (760 Torr)
• Flash Point: 94.7±25.1℃
• Appearance: /
• Density: 1.38±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 4.55±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 3-(3-Methyl-3H-diazirine-3-yl)propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-Methyl-3H-diazirine-3-yl)propionic acid(25055-86-1)
• EPA Substance Registry System: 3-(3-Methyl-3H-diazirine-3-yl)propionic acid(25055-86-1)

Safety Data

• Hazardous Substances Data: 25055-86-1(Hazardous Substances Data)

Usage

Description

3-(3-methyl-3H-diazirine-3-yl)propionic acid, also known as 3-methyl-diazirine-3-propanoic acid, is a chemical compound that features a diazirine functional group. This unique structure endows it with properties that make it highly reactive and useful in various chemical and biological applications. It is particularly known for its ability to form covalent bonds with other molecules upon exposure to light, which is a key feature in its utility.

Uses

Used in Chemical Research:
3-(3-methyl-3H-diazirine-3-yl)propionic acid is used as a reagent for crosslinking sugars. Its photoreactive nature allows it to form stable covalent bonds with sugar molecules upon exposure to light, which is crucial for studying the structure and function of glycoconjugates and other sugar-containing biomolecules.
Used in Photoactivatable Crosslinking:
In the field of molecular biology and biochemistry, 3-(3-methyl-3H-diazirine-3-yl)propionic acid is utilized as a photoactivatable crosslinking agent. This application takes advantage of its ability to form covalent bonds with target molecules when activated by light. This property is particularly useful in techniques such as photo-crosslinking chromatin immunoprecipitation (photo-XChIP), where it helps in studying protein-DNA interactions in a controlled manner.
Used in Pharmaceutical Development:
3-(3-methyl-3H-diazirine-3-yl)propionic acid may also find use in the development of drugs that target specific biomolecules through covalent bonding. Its reactivity can be harnessed to design drugs that irreversibly bind to their targets, potentially increasing the potency and selectivity of therapeutic agents.
Used in Materials Science:
In the realm of materials science, 3-(3-methyl-3H-diazirine-3-yl)propionic acid could be employed in the development of novel materials with specific properties. Its ability to form covalent bonds can be used to create crosslinked networks or to attach functional groups to various substrates, tailoring the material's characteristics for specific applications.
Overall, the versatility of 3-(3-methyl-3H-diazirine-3-yl)propionic acid stems from its unique photoreactive diazirine group, which allows it to be a valuable tool in various scientific disciplines.

Upstream product

• 16297-94-2 3-(3-Methyldiazirin-3-yl)propan-1-ol 
• 3128-06-1 5-ketohexanoic acid 
• 123-76-2 levulinic acid 
• 1186308-36-0 3-(3-methyldiaziridin-3-yl)propanoic acid 
• 1255731-57-7 3-(3-methyl-3H-diaziren-3-yl)propanenitrile 
• 1071-73-4 5-Hydroxy-2-pentanone 

Downstream Products

• 591-80-0 pent-4-enoic acid 
• 33698-87-2 (Z)-pent-3-enoic acid 
• 1617-32-9 (E)-3-pentenoic acid 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 1255731-92-0 N-cyclohexyl-N₂-[3-(3-methyl-3H-diaziren-3-yl)propanoyl]-N₂-(1-methylethyl)phenylalaninamide 
• 1255731-61-3 1-benzyl-2-(tert-butylamino)-2-oxoethyl 3-(3-methyl-3H-diaziren-3-yl)propanoate 
• 1255731-90-8 N₂-benzyl-N-tert-butyl-N₂-[3-(3-methyl-3H-diaziren-3-yl)propanoyl]valinamide 
• 1620482-67-8 N-[1-(1-benzyl-1H-tetrazol-5-yl)-3-methylbutyl]-3-(3-methyl-3H-diaziren-3-yl)-N-(2-propyn-1-yl)propanamide 
• 1620482-69-0 N-{(1-cyclohexyl-1H-tetrazol-5-yl)[4-(dimethylamino)phenyl]methyl}-3-(3-methyl-3H-diaziren-3-yl)-N-(2-propyn-1-yl)propanamide 
• 1620482-73-6 N-[(1-butyl-1H-tetrazol-5-yl)(4-ethynylphenyl)methyl]-N-(2-methoxyethyl)-3-(3-methyl-3H-diaziren-3-yl)propanamide 
• 1620483-05-7 N-[(1-butyl-1H-tetrazol-5-yl)(4-methoxyphenyl)methyl]-3-(3-methyl-3H-diaziren-3-yl)-N-propylpropanamide 
• 27162-81-8 N-benzyl-3-(3-methyl-3H-diazirin-3-yl)-propionamide 
• 1255731-94-2 N-[2-(2,2-dimethoxyethyl)phenyl]-N₂-[3-(3-methyl-3H-diaziren-3-yl)propanoyl]-N₂-(1-methylethyl)valinamide 
• 25055-90-7 3-(3-methyl-3H-diazirin-3-yl)propanoyl chloride 

Relevant articles and documents

Improved synthesis of photo-leucine

An improved and reproducible synthesis of photo-leucine [3-(3-methyl-3-diazirinyl)-alanine] is presented. Copyright Taylor & Francis Group, LLC.

Diazirine-containing photoactivatable isoprenoid: Synthesis and application in studies with isoprenylcysteine carboxyl methyltransferase

Photoaffinity labeling is a useful technique employed to identify protein-ligand and protein-protein noncovalent interactions. Photolabeling experiments have been particularly informative for probing membrane-bound proteins where structural information is difficult to obtain. The most widely used classes of photoactive functionalities include aryl azides, diazocarbonyls, diazirines, and benzophenones. Diazirines are intrinsically smaller than benzophenones and generate carbenes upon photolysis that react with a broader range of amino acid side chains compared with the benzophenone-derived diradical; this makes diazirines potentially more general photoaffinity-labeling agents. In this article, we describe the development and application of a new isoprenoid analogue containing a diazirine moiety that was prepared in six steps and incorporated into an a-factor-derived peptide produced via solid-phase synthesis. In addition to the diazirine moiety, fluorescein and biotin groups were also incorporated into the peptide to aid in the detection and enrichment of photo-cross-linked products. This multifuctional diazirine-containing peptide was a substrate for Ste14p, the yeast homologue of the potential anticancer target Icmt, with Km (6.6 μM) and Vmax (947 pmol min-1 mg-1) values comparable or better than a-factor peptides functionalized with benzophenone-based isoprenoids. Photo-cross-linking experiments demonstrated that the diazirine probe photo-cross-linked to Ste14p with observably higher efficiency than benzophenone-containing a-factor peptides.

One-Pot Synthesis of Diazirines and 15N2-Diazirines from Ketones, Aldehydes and Derivatives: Development and Mechanistic Insight

Broad scope one-pot diazirine synthesis strategies have been developed using two different oxidants depending on the nature of the starting material. In all cases, an inexpensive commercial solution of ammonia (NH3) in methanol (MeOH) was emplo

PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS

Photoactive probes and probe systems for detecting biological interactions are described. The photoactive probes include probes that combine both photocleavable and photoreactive moieties. The photoactive probe systems can include a first probe comprising a photocatalytic group and a second probe comprising a group that can act as a substrate for the reaction catalyzed by the photocatalytic group. The probes and probe systems can also include groups that can specifically bind to a binding partner on a biological entity of interest and a detectable group or a precursor thereof. The probes and probe systems can detect spatiotemporal interactions of proteins or cells. In some embodiments, the interactions can be detected in live cells. Also described are methods of detecting the biological interactions.