25055-86-1

Usage

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

• 123-76-2 levulinic acid 
• 16297-94-2 3-(3-Methyldiazirin-3-yl)propan-1-ol 
• 1186308-36-0 3-(3-methyldiaziridin-3-yl)propanoic acid 
• 3128-06-1 5-ketohexanoic 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 
• 27162-81-8 N-benzyl-3-(3-methyl-3H-diazirin-3-yl)-propionamide 
• 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 
• 1620483-10-4 (1-[4-(1-benzyl-1H-tetrazol-5-yl)-4-(propylamino)-1-piperidinyl]-3-(3-methyl-3H-diaziren-3-yl)-1-propanone) 
• 1620482-68-9 1-[4-(1-benzyl-1H-tetrazol-5-yl)-4-(2-propyn-1-ylamino)-1-piperidinyl]-3-(3-methyl-3H-diaziren-3-yl)-1-propanone 

Relevant academic research and scientific papers

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.

Selective profiling of steviol-catalyzing UDP-glycosyltransferases with a metabolically synthesized probe

Selective profiling of steviol-catalyzing UDP-glycosyltransferases in plants was accomplished with a probe metabolically synthesized from two substrate-derived components comprising an alkynylated sugar receptor (steviol) module and a diazirine-modified sugar donor (UDP-glucose) module, thereby illustrating a facile approach for harnessing biosynthetic enzymes of natural glycosides in plants for synthetic biology.

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.

Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming

Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production. In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chemistry-based probe strategy. Erianin potently inhibited the enzymatic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Analysis of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC.

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

Traceless Staudinger Ligation to Introduce Chemical Diversity on β-Lactamase Inhibitors of Second Generation

We explored the traceless Staudinger ligation for the functionalization of the C2 position of second generation β-lactamase inhibitors based on a diazabicyclooctane (DBO) scaffold. Our strategy is based on the synthesis of phosphine phenol esters and thei

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.

Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis

Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.

Compounds and methods of use

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein X1, X2, X3, X4, Y, A, L1, L2, R1, R2, R5, m and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Photosensitive molecule and preparation method of surface-enhanced Raman detection substrate containing same

The invention discloses a photosensitive molecule for constructing a photoresponse soft and hard substrate, and the structural general formula is as shown in the specification. R1 - X-R2 . and, The invention further discloses a prepa