The preparation of cross-linked nanosheets with 1–2 nm thickness and predefined shape was achieved by lithographic immobilization of trimethacryloyl thioalkanoates onto the surface of Si wafers, which were functionalized with 2-(phenacylthio)acetamido groups via a photoinduced reaction. Subsequent cross-linking via free radical polymerization as well as a phototriggered Diels–Alder reaction under mild conditions on the surface led to the desired nanosheets. Electrospray ionization mass spectrometry (ESI-MS), X-ray photoelectron spectroscopy (XPS), time-of-flight secondary ion mass spectrometry (ToF-SIMS), as well as infrared reflection-absorption spectroscopy (IRRAS) confirmed the success of individual surface-modification and cross-linking reactions.
ESI-MS analysis was performed using the Advion Interchim Scientific® expression® Compact Mass Spectrometer (CMS).
A convenient one-pot, multi-component and solvent free procedure for the preparation of substituted 2-amino-5-aryl-1,3,4-oxadiazoles has been achieved. The method is a significant improvement over previously reported synthesis. Reaction of acid chlorides with hydrazine hydrate and isothiocynates under microwave-irradiation (MWI) afforded the corresponding 1,3,4-oxadiazole derivatives in high yields with high purity. All synthesized compounds were characterized by FT-IR, proton and carbon NMR, mass spectroscopy and elemental analysis. A possible mechanism is proposed for the cyclodesulfurization based on the results of this study.
Mass spec analysis was performed on the Advion expression Compact Mass Spectrometer (CMS) using electrospray ionization (ESI).
Guru Ghasidas University, University of South Dakota
A one-pot practical, efficient, and environmentally benign multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications has been developed using a very mild, neutral, and reusable silica nanoparticles as catalyst. The 4H-pyran derivatives were synthesized by a three component reaction of an aldehyde, malononitrile, and 5,5-dimethyl-1,3-cyclohexanedione or ethyl acetoacetate at room temperature or refluxing in ethanol. Alternatively, polysubstituted anilines were synthesized via a four component reaction of an aldehyde, a ketone, and two equivalents of malononitrile in ethanol.
Mass spec analysis was carried out using an Advion expression Compact Mass Spectrometer (CMS).
University of Surrey, Surrey and Borders Partnership NHS Foundation Trust, Advion, Ltd.
Abstract
Surface mass spectrometry methods can be difficult to use effectively with low cost, portable mass spectrometers. A new analytical method is presented where analytes are extracted from a sample using a solvent flushed across the surface under high pressure, separated using a chromatography column and then analysed using the Advion Interchim Scientific® expression® Compact Mass Spectrometer (CMS). In this publication, we demonstrate the efficacy of the method for the quantitative detection of cocaine and benzoylecgonine in urine and oral fluid.
In this note, a quick and direct screening method for the detection of illicit drugs on paper currency is introduced using the Touch Express™ Open Port Sampling Interface (OPSI) on the Advion expression® Compact Mass Spectrometer (CMS).A range of paper currency bills from different countries were analyzed for traces of illicit drugs.
Learn how SpiroChem AG (Switzerland) utilized the Advion expression® Compact Mass Spectrometer (CMS) and Plate Express™ TLC Plate Reader for reaction monitoring and compound identification to aide in accelerating drug discovery.
Abstract:
In highly competitive research environments, the ability to access more complex structural spaces efficiently is a predictor of a company’s ability to generate novel IP-protected small molecule candidates with adequate properties, hence filling their development pipelines. SpiroChem is consistently developing new synthetic methodologies and strategies to access complex molecular structure, thereby facilitating and accelerating small molecule drug discovery. Pushing the limits of what are perceived as complex molecular structures allows SpiroChem and its clients to unleash creativity and explore meaningful chemical spaces, which are under-exploited sources of novel active molecules. In this article, we [SpiroChem] explain how we differentiated ourselves in a globalized R&D environment and we provide several snapshots of how efficient methodologies can generate complex structures, rapidly.
A: The Rappsilber Laboratory is interested in studying the machinery of life, in particular protein structures and their interactions in living cells. Determining protein behaviour is crucial for developing new drugs or understanding terrible diseases such as cancer. We are doing this by developing state-of-the-art methods and new chemical tools for crosslinking mass spectrometry (crosslinking-MS), including new crosslinker reagents and crosslinking chemistry. Working on the chemistry-biology interface, our work encompasses chemical synthesis of peptides, fluorophore tagged sensors, peptide- and protein-reactive crosslinking reagents and bioorthogonal metal catalysts.
Q: WHAT WAS YOUR PREVIOUS WORKFLOW OR CHALLENGES?
A: This year (2020) we built a chemistry lab from scratch, here at the Institute of Biotechnology (TU Berlin). We had the opportunity to really think about our work flow requirements and create the most efficient chemical synthesis pipeline for a modern, 21st century, small chemistry laboratory. However, we are a satellite campus, located more than 10 km from the Institute of Chemistry, which meant that we were constrained by the lack of usual chemistry infrastructure. One of the major challenges that we faced here, is that without chemistry-specific analytical capability, we are working almost blind. Every step of chemical synthesis, including reaction monitoring, work-up, purification and final product characterisation required an exhausting and disruptive journey across Berlin!
Q: WHY DID YOU INCORPORATE THE EXPRESSION® CMS INTO YOUR LABORATORY?
A: We operate an advanced proteomics facility, with cutting edge, high-precision, high sensitivity mass spectrometers for analysing extremely complex peptide mixtures. But a chemist needs a workhorse, not a Formula 1 car. The Advion Interchim Scientific expression® CMS was a no-brainer. We needed a system that is versatile, compact, easy-to-use, easy-to-maintain (~10 minute calibration), robust and allows fast analysis (result in <30 seconds). This system is all of this, but furthermore it is a delight to use. The ASAP® Direct Analysis Probe works fantastically well for analysis of solids and liquids. Switching between APCI and ESI is so quick and easy. The Plate Express® system makes it a joy to identify reaction products directly from TLC plates, greatly simplifying subsequent purifications. The Plate Express™ also works really well for identifying synthesized peptides from TLC spots. The expression® CMS sits at the heart of our chemistry lab and workflow.
Q: WHO WOULD YOU RECOMMEND TO PURCHASE THE EXPRESSION® CMS?
A: We would recommend the Advion Interchim Scientific expression® CMS to literally any research laboratory, big or small. The versatility of the system is truly impressive.
A: The research of the new Institute for Drug Discovery seeks to combine computational and experimental efforts to investigate proteins and their interactions with small molecule substrates. The Medicinal Synthetic Chemistry Core is part of the new institute and responsible for the synthesis of potentially bio-active compounds based on the computational results predicting a high binding affinity to the proteins’ active sites.
Q: WHAT WAS YOUR PREVIOUS WORKFLOW OR CHALLENGES?
A: Previously, we separated all unknown by-products of our synthesis in order to investigate their structure based on NMR and external mass spec service. This time wasting workflow often resulted in a dead-end strategy with low efficiency.
Q: WHY DID YOU INCORPORATE THE expression® CMS INTO YOUR LABORATORY?
A: Since the purchase of the CMS, we improved our strategic synthesis planning extraordinarily. By using Plate Express™ as TLC-Interface together with the expression® CMS, the by-products could become quickly separated on TLC-plates and directly analyzed by mass spectrometry afterwards. Now we see it, now we know it, and we get it quickly purified.
Q: WHO WOULD YOU RECOMMEND TO PURCHASE THE expression® CMS?
A: I will highly recommend the CMS to all research institutes with a strong synthetical and natural product background of small molecules.
Successfully completing an organic synthesis involves three typically lengthy, but crucial steps: reaction monitoring, compound identification, and purification. These steps can create bottlenecks in the synthesis, unless a purpose-built, streamlined, and reliable workflow is on hand.
This whitepaper delves into some of the challenges faced by synthetic organic chemists as they navigate compound identification and purification struggles. It also describes how using a workflow that couples thin layer chromatography (TLC) and mass spectrometry (MS) to flash purification can help increase the efficiency of the entire process.
Key Objectives：
Understand how a workflow that combines thin-layer chromatography, mass spectrometry, and flash purification can increase the speed and efficiency of an entire organic synthesis process.
Learn about prep-free techniques that have become the new standard: scraping TLC spots, developing flash methods and performing long liquid chromatography/MS runs are not necessary with modern instrumentation that is specifically developed to take the prep-work and guess-work out of the purification process.
Become informed about a cost-effective, user-friendly benchtop workflow solution for organic compound identification and purification that can save time and money for any lab.
Rey Juan Carlos University, Complutense University of Madrid, University Rennes
Abstract
Lichens produce unique secondary metabolites with a rich potential as bioactive compounds. In many cases, the use of these molecules is limited by the low concentration of these compounds in thalli, low growth rate in culture, and changes in chemical patterns between thalli and aposymbiotic culture. In addition, the massive collection of some species of industrial interest can cause damage to lichen diversity and the associated environment. Six lichenized fungi (Arctoparmelia centrifuga, Parmelia saxatilis, Parmelina tiliacea, Platismatia glauca, Xanthoparmelia tinctina, and Usnea ghattensis) with biotechnological interest and belonging to Parmeliaceae have been cultured in order to test culture conditions and obtain enough biomass for further studies. In addition, we analyzed the compounds synthetized in axenic conditions and they were compared with chemosyndromes identified in complete thalli. Arctoparmelia centrifuga, P. saxatilis, P. tiliacea and X. tinctina were successfully cultivated while for P. glauca and U. ghattensis we only obtained sporulation and germination of the spores. The chemical pattern of the compounds secreted into the culture media varied significantly from the chemosyndrome of the whole thallus. Phenolic compounds of pharmacological and industrial interest (usnic acid, aspicilin, α-alectoronic acid, physodic acid, lobaric acid and nordivaricatic acid) and a wide variety of potentially bioactive compounds were obtained during the culture process.
Analysis was performed by LC/MS using the Advion Interchim Scientific® expression® Compact Mass Spectrometer (CMS).
