Name: (4S)-4-Azido-L-proline
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

(S)-4-Azido-L-proline; H-Pro(4-N3) (2S,4S); H-L-Pro(4-N3) (2S,4S); H-L-Pro(4-N3)-OH (2S,4S); H-Pro(4-N3)-OH (2S,4S); (2S,4S)-H-L-Pro(4-N3)-OH

IUPAC Name

(2S,4S)-4-azidopyrrolidine-2-carboxylic acid

Canonical SMILES

C1[C@@H](CN[C@@H]1C(=O)O)N=[N+]=[N-]

InChI

InChI=1S/C5H8N4O2/c6-9-8-3-1-4(5(10)11)7-2-3/h3-4,7H,1-2H2,(H,10,11)/t3-,4-/m0/s1

InChIKey

PPRFZPZRQYPCER-IMJSIDKUSA-N

Melting Point

147-154°C

Appearance

White or off-white crystalline powder

Storage

Store at 2-8 °C

(4S)-Azido-L-Proline hydrochloride, a versatile compound with diverse applications in biochemical and pharmaceutical research, serves as a cornerstone in various scientific fields. Here are four key applications presented with high perplexity and burstiness:

Chemical Biology: At the intersection of chemistry and biology, (4S)-Azido-L-Proline hydrochloride finds its niche as a tool for the site-specific labeling of proteins. Its azido group facilitates click chemistry reactions, allowing for precise tagging and probing of proteins. Researchers leverage this capability to delve into protein interactions and follow protein localization dynamics within cells with intricate detail.

Peptide Synthesis: In the realm of peptide synthesis, (4S)-Azido-L-Proline plays a critical role in crafting modified peptides for structural and functional analyses. By integrating this compound into peptides, scientists can introduce functional motifs for subsequent biochemical modifications, creating peptides with tailored stability, activity, or targeting characteristics. This versatility is essential for the design of peptides with specialized functionalities.

Drug Discovery: Positioned at the forefront of drug development, (4S)-Azido-L-Proline hydrochloride contributes to the creation of innovative drug candidates. Its distinctive structure is incorporated into small molecule libraries for expansive screening against diverse biological targets. This screening process aids in the identification of potential therapeutic agents with efficacy and specificity, driving forward the discovery of novel treatments.

Protein Engineering: Harnessing the power of (4S)-Azido-L-Proline hydrochloride in protein engineering opens doors to the incorporation of non-natural amino acids into proteins. This modification enables the exploration of protein folding, stability, and function, leading to the creation of proteins with novel attributes. By expanding the toolbox for synthetic biology and biotechnological applications, this application broadens the horizons of protein engineering possibilities.

1. Lurasidone: efficacy and safety in the treatment of psychotic and mood disorders

Maurizio Pompili, et al. Expert Opin Drug Saf. 2018 Feb;17(2):197-205. doi: 10.1080/14740338.2017.1379989. Epub 2017 Sep 26.

Lurasidone ([3aR,4S,7R,7aS]-2-[(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1yl-methyl] cyclohexylmethyl]-hexahydro-4,7-methano-2H-isoindole-1,3-dione hydrochloride; Latuda®) is a novel benzisothiazole, second-generation antipsychotic drug developed by Dainippon Sumitomo Pharma Corporation in Japan. Similar to other atypical antipsychotics it has a distinctive pharmacodynamic profile, Areas covered: This review updates reported research findings on the efficacy, safety and tolerability of LRSD for treatment of psychotic and major affective disorders, with meta-analyses. Short-term efficacy of LRSD in schizophrenia is supported by several randomized, controlled trials with daily doses of 40-160 mg, yielding relatively modest symptomatic improvements. Lurasidone has regulatory approval for treatment of undefined duration in schizophrenia. Long-term benefits and effects in schizophrenia, and both short- and long-term use for other psychotic disorders and mania have not been tested. LRSD shows unusual efficacy in acute bipolar depression even without psychotic features. However, trials of adding LRSD to lithium or valproate for bipolar disorder have yielded inconsistent findings. Expert opinion: Available research findings indicate that LRSD is effective and well-tolerated for short-term treatment of schizophrenia, and for acute bipolar depression. It has low risk of inducing weight-gain, metabolic, or cardiac abnormalities, but its risk of akathisia may exceed that of other modern antipsychotics. Needed is adequate long-term testing in schizophrenia and bipolar disorder and testing for other indications, including against alternative treatments.

2. Localised plasmonic hybridisation mode optical fibre sensing of relative humidity

LiangLiang Liu, Serhiy Korposh, David Gomez, Ricardo Correia, Barrie R Hayes-Gill, Stephen P Morgan Sens Actuators B Chem. 2022 Feb 15;353:131157. doi: 10.1016/j.snb.2021.131157.

This work reports an optical fibre probe functionalised with 'cotton-shaped' gold-silica nanostructures for relative humidity (RH) monitoring. The sensor response utilises the localised surface plasmon resonance (LSPR) of self-assembled nanostructures: gold nanospheres (40 nm) surrounded by one layer of poly (allylamine hydrochloride) and hydrophilic silica nanoparticles (10-20 nm) on the end-facet of an optical fibre via a wavelength shift of the reflected light. Sensor optimisation is investigated by varying the density of gold nanoparticles on the end-facet of an optical fibre. It is demonstrated that the plasmonic hybridisation mode appearing when the average gold interparticle distance is small (Median: 7.5 nm) is more sensitive to RH after functionalisation than the singular plasmonic mode. The plasmonic hybridisation mode sensor demonstrates a high linear regression to RH with a sensitivity of 0.63 nm/%RH and excellent reversibility. The response time (T10-90%) and recovery time (T90-10%) are calculated as 1.2 ± 0.4 s and 0.95 ± 0.18 s. The sensor shows no measurable cross-talk to temperature in the tested range between 25 °C to 40 °C and the 95% limit of agreement is 3.1%RH when compared to a commercial reference sensor. Simulation with finite element analysis reveals a polarisation-dependent plasmonic hybridisation with a redshift of plasmonic wavelength as a decrease of the interparticle distance and a higher refractive index sensitivity, which results in a high sensitivity to RH as observed in the experiment.

3. A Carbocationic Triarylmethane-Based Porous Covalent Organic Network

Sunny K S Freitas, Felipe L Oliveira, Thiago C Dos Santos, Danilo Hisse, Claudia Merlini, Célia M Ronconi, Pierre M Esteves Chemistry. 2021 Feb 1;27(7):2342-2347. doi: 10.1002/chem.202003554. Epub 2020 Dec 23.

A thermally stable carbocationic covalent organic network (CON), named RIO-70 was prepared from pararosaniline hydrochloride, an inexpensive dye, and triformylphloroglucinol in solvothermal conditions. This nanoporous organic material has shown a specific surface area of 990 m2 g-1 and pore size of 10.3 Å. The material has CO2 uptake of 2.14 mmol g-1 (0.5 bar), 2.7 mmol g-1 (1 bar), and 6.8 mmol g-1 (20 bar), the latter corresponding to 3 CO2 molecules adsorbed per pore per sheet. It is shown to be a semiconductor, with electrical conductivity (σ) of 3.17×10-7 S cm-1 , which increases to 5.26×10-4 S cm-1 upon exposure to I2 vapor. DFT calculations using periodic conditions support the findings.