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Organic synthesis toward small-molecule probes and …

Looks like a pretty neat paper. You are echoing something that George Whitesides has often said (which I blogged about – linked in my handle): Chemists need to move beyond the molecule. Organic synthesis has become commoditized and is no longer the creative frontier in chemistry. Chemists need to find new pastures to fertilize if they want to truly push the boundaries of their science.
But in some sense synthesis should be proud of itself for getting to this state of affairs, since this is what happens when a science becomes a victim of its own success, when its vital processes become so fine-honed and standardized that an undergraduate (or a chemist in China or India) can do them in an afternoon. So let’s wear that badge with honor and move on to the next battlefield.

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The mechanism of action seems to be related to impaired protein synthesis.

Evaluating enzymatic synthesis of small molecule drugs

Membrane-like structure in cell cytoplasm; site of protein synthesis  Endothelium.

Anybody understand the 1.5% MeOH/Et2O does not elute, THF does elute behavior of MIDA boronates, and care to enlighten this aging chemist? Seems a bit odd.
Also, if ALL the MIDA boronates stick, and are then eluted, won’t any unreacted MIDA boronate carry on to the next reaction? Asked another way, how does one ensure that all the MIDA boronate is consumed in the first reaction? (In nucleotide synthesis, it is by vast excess of one reagent, if I recall correctly.)

Florent received his Ph.D. in Organic Chemistry at the University of Bern in 2004, and carried out postdoctoral work on total synthesis with Alois Fürstner at the Max Planck Institute für Kohlenforschung in 2005. He was Head of Chemistry and Quality Control at Covalys Biosciences AG (Switzerland) (2005 - 2009), Senior Researcher at the Department of Biomedicine of the University of Basel (2009 - 2012) and Deputy Head of Chemistry at PIQUR Therapeutics AG (2012 - 2016).

Assembling an initial list of candidate molecules.

#28 – The MIDA boronates themselves are unreactive. However, they are readily cleaved to the corresponding boronic acids under mild aqueous basic conditions. In The Machine, the MIDA boronate is dissolved up in water with NaOH, hydrolyses, and is then subjected to the cross-coupling.
I guess that means the reactive species (boronic acid) will be eluted in the 1.5% MeOH/ether stage of purification. I suppose if the initial hydrolysis is not quantitative, then you could have that issue of remnant MIDA boronate in the following steps.
Then again, that would only be an issue if you were making something novel. If you could use this process for automated synthesis of known compounds, the conditions could be optimised. The whole thing is essentially run by computer – just tell the computer what quantities/temperatures/reaction times are best for a particular known synthesis, and it can do the rest.

I like the angle of democratizing synthesis, albeit for a limited range of compounds. There is a hell of a lot of basic work that can be done with this type of approach, even if it needs to be refined with *real* chemistry later on.

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Molecules | Free Full-Text | Synthesis and ..


Custom Synthesis | SpiroChem | Tailor-Made Molecules

After several years working as a business developer at a French CRO specialized in organic chemistry and custom synthesis, she joined the SpiroChem team to support business and marketing development.

Synthesis of biologically active molecules - Purdue …

When you listen to his talks Burke IS persuasive, but then reflecting on the real impact on small molecule SAR chemistry … doubt is getting the best of this concept. Peptides and nucleotides are made via one single connection from a rather limited number of building blocs. No way this approach will prove useful for the diversity of organic building blocks and bond types available to the organic chemist. Being mean: this is the defrosted version of “high throughput paralell synthesis” – anybody seen something useful coming out of that hype ever ?
It’s nice work, no doubt – congrats to Burke, will chip the best out of nanomaterials and other dendirmers, but get your brains working again. There are receptors waiting for your molecules …

Synthesis of biologically active molecules

Polarized cells such as epithelia maintain distinct apical and basolateral plasma membrane domains with distinct protein and lipid compositions. These specializations of the plasma membrane require complex membrane trafficking pathways thought to include unique basolateral versus apical sorting mechanisms in the secretory pathway to direct newly synthesized proteins to the correct membrane domain. Additional regulation of the endocytosis pathway maintains polarity of lipid and protein components after internalization and recycling.

The molecular mechanism of ATP synthesis by F1F0 …

Wow, interesting stuff, but let’s not get so excited. I was going to say a lot more, but others such as David Borhani (#22) have said exactly what I had in mind.
Derek, you need to think about this some more, re-read some of the old ‘exciting’ articles on solid phase organic synthesis and consider what that revolution led us to, and then post your reassessment with an apology.

Organic synthesis of bioactive molecules Research …

One component of the general secretory pathway that has been studied in significant detail in is , a part of the endoplasmic reticulum vesicle coat complex known as COPII (). COPII is known to be the primary vesicle coat complex used in yeast and mammalian cell transport from the ER to the Golgi. Roberts et al. identified a single mutant allele of in a screen for embryonic lethals defective in cuticle synthesis as assayed by a cuticle collagen reporter, (). These authors went on to show severe defects in cuticle synthesis in mutants resulting in accumulation of collagen intracellularly, presumably in the ER. Zygotic embryonic lethality during elongation was found in homozygous mutants derived from heterozygous mothers. Normal progression through early development presumably relies upon maternally derived . RNAi experiments revealed a requirement for during larval development, particularly during molting. Adults depleted of by RNAi also showed severe germline defects including binucleate oocytes, lack of yolk uptake by oocytes resulting from a failure of yolk receptors () to reach the cell surface, and premature maturation/partitioning of individual germ cells, possibly resulting from loss of cell surface receptors in the distal gonad. A partially functional ::GFP reporter gene indicated that is broadly expressed at all life stages, and that in hypodermal cells the protein is concentrated in distinct foci. In the embryonic hypodermis these foci were enriched apically at the periphery of the endoplasmic reticulum. These positive foci likely represent ER exit sites where newly synthesized cargo molecules concentrate and are packaged into COPII coated vesicles for delivery to the Golgi.

View Organic synthesis of bioactive molecules Research Papers on ..

Wow, a lot of hate for this work here in the comments. I agree with Derek’s perspective though and it makes me (an organic chemistry PhD candidate) sad and kind of worried. Sad that this field that I love might one day be thought of the way I think about peptide coupling chemistry (Ech!). Worried that my job prospects might be highly limited in 20 years time.
This is clearly very good work and I think people need to understand that this is not the final product, but rather a proof of concept that, for the first time, shows that fully automated synthesis is entirely possible. Yes, the process is limited to sp2-sp2 (and primary sp3) coupling at the moment and we haven’t yet made an infinite catalog of BMIDA compounds, but these are only challenges that will eventually be overcome. The battle has only just begun, but it has already been won. Cheers to Burke and his students though, truly fantastic work.

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