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Offlineblackout
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‘Magic mushroom’ enzyme mystery solved
    #24553639 - 08/14/17 06:23 PM (3 years, 8 months ago)

http://cen.acs.org/articles/95/web/2017/08/Magic-mushroomenzyme-mystery-solved.html

Quote:

‘Magic mushroom’ enzyme mystery solved
Researchers unravel the biosynthesis of the psychoactive drug psilocybin, making large-scale production a possibility
By Stephen K. Ritter

The euphoria and hallucinations induced from eating Psilocybe “magic mushrooms” have earned the fungi a cult following. Sandoz chemist Albert Hofmann isolated and determined the structure of psilocybin, the main ingredient in mushrooms that leads to the psychedelic effects, nearly 60 years ago. That discovery and subsequent mind-altering experiments by Harvard University psychologist Timothy F. Leary have left scientists longing to develop a large-scale synthesis of the compound for medical uses, which include treating anxiety and depression in terminal cancer patients and treating nicotine addiction. Yet no one has been able to unravel the enzymatic pathway the mushrooms use to make psilocybin, until now.
Janis Fricke, Felix Blei, and Dirk Hoffmeister of Friedrich Schiller University Jena have identified and characterized to the greatest extent so far the four enzymes that the mushrooms use to make psilocybin. The team then developed the first enzymatic synthesis of the compound, setting the stage for its possible commercial production (Angew. Chem. Int. Ed. 2017, DOI: 10.1002/anie.201705489).
During their study, Hoffmeister and coworkers sequenced the genomes of two mushroom species to identify the genes that govern fungal enzymatic production of psilocybin. They further used engineered bacteria and fungi to confirm the gene activity and exact order of synthetic steps. This process includes a newly discovered enzyme that decarboxylates tryptophan, an enzyme that adds a hydroxyl group, an enzyme that catalyzes phosphorylation, and an enzyme that mediates two sequential amine methylation steps. With that knowledge in hand, the team designed a one-pot reaction using three of the enzymes to prepare psilocybin from 4-hydroxy-L-tryptophan.
Medicinal chemist Courtney Aldrich of the University of Minnesota, Twin Cities, praises Hoffmeister and his coworkers for their painstaking efforts to elucidate the biosynthesis of psilocybin. “Our knowledge of the biosynthesis of fungal natural products has lagged behind our understanding of the corresponding bacterial biosynthetic pathways owing to a number of unique challenges,” Aldrich says. These include greater genome complexity in fungi compared with bacteria, many fungi are still not amenable to genetic manipulation, and cultivating fungi to produce sufficient amounts of desired metabolites is not always straightforward. “The new work lays the foundation for developing a fermentation process for production of this powerful psychedelic fungal drug, which has a fascinating history and pharmacology,” Aldrich adds.
“The publication by Hoffmeister and colleagues highlights a terrific example of genomics-based biocatalyst-pathway discovery,” adds natural products researcher Jon S. Thorson of the University of Kentucky. “While psilocybin biosynthesis derives from a series of fairly simple chemical transformations, this new study identifies the contributing genes and biocatalysts for the first time and, importantly, provides strong evidence to support a revision of the order of the key steps proposed more than five decades ago. This work clearly sets the stage for bioengineered psilocybin production and/or for analogs that may serve as compelling alternatives to existing synthetic strategies.”




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Offlinemusiclover420
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: blackout]
    #24553721 - 08/14/17 06:58 PM (3 years, 8 months ago)

:awesomenod:

How long until we have synthetic bacteria for farming Psilicybin?

Imagine trading various strains of genetically engineered organisms for mass producing psilocybin :crazy2:

Would be crazy to see something similar applied to DMT and LSA or even mescaline.


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Edited by musiclover420 (08/14/17 06:58 PM)


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OfflineTheHulk69
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: musiclover420]
    #24553777 - 08/14/17 07:19 PM (3 years, 8 months ago)

I  mean don't get me wrong... This is pretty rad.

But isn't it kinda silly? I mean growing clean mushrooms is fairly easy.

Though I suppose extracting psilocybin from them is a bit more nuanced.. I suppose a "pharmaceutical" psilocybin has better research potential, and ease of dosage


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Offlinemusiclover420
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: TheHulk69]
    #24553822 - 08/14/17 07:36 PM (3 years, 8 months ago)

It could be useful for research too perhaps.

They could make bacteria or fungi that produces higher concentrations of specific chemicals.

Like psilocin or psilocybin as well as baeocybin and whatever that other one is :lol:


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Re: ‘Magic mushroom’ enzyme mystery solved [Re: musiclover420]
    #24553835 - 08/14/17 07:40 PM (3 years, 8 months ago)

Love having a friend in med school, just got the official manuscript. This article is charging just to view that shit lol.


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Offline24sevenZed
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Inspir3]
    #24553968 - 08/14/17 08:29 PM (3 years, 8 months ago)

What I find more interesting about this is that it could allow one to develop knock out methods for these enzymes in, e.g. Psilocybe Cubensis, and to finally trade Cubensis (and other psilocybe) cultures legally.


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OfflineNature Boy
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: 24sevenZed]
    #24554154 - 08/14/17 09:26 PM (3 years, 8 months ago)

The line that caught my attention was the one that said "an enzyme that mediates two sequential amine methylation steps."  This infers that there is the potential for a wholly enzymatic synthesis of dimethyltryptamine (DMT).  Would love to read the paper that sets THAT process out in detail.  :super:


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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Nature Boy]
    #24554189 - 08/14/17 09:36 PM (3 years, 8 months ago)

Quote:

Nature Boy said:
The line that caught my attention was the one that said "an enzyme that mediates two sequential amine methylation steps."  This infers that there is the potential for a wholly enzymatic synthesis of dimethyltryptamine (DMT).  Would love to read the paper that sets THAT process out in detail.  :super:



meaning it allows step 2 to go to step 4, skipping 3?


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Invisible36fuckin5
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: 24sevenZed]
    #24554303 - 08/14/17 10:09 PM (3 years, 8 months ago)

Quote:

24sevenZed said:
What I find more interesting about this is that it could allow one to develop knock out methods for these enzymes in, e.g. Psilocybe Cubensis, and to finally trade Cubensis (and other psilocybe) cultures legally.




Why is that interesting? The only cool things about Psilocybes are that they're active. Take that away and they're not worth eating.


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Offline24sevenZed
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: 36fuckin5]
    #24554492 - 08/14/17 11:31 PM (3 years, 8 months ago)

Quote:

36fuckin5 said:
Why is that interesting? The only cool things about Psilocybes are that they're active. Take that away and they're not worth eating.




I think cubensis is probably the most widely grown (by amateurs) mushroom in the world second only to Oysters (I doubt it). The accumulated knowledge available on the Shroomery for this species alone is incredible. Imagine if that knowledge could be utilized by people who just want to learn about mushrooms without all the legal bullshit?


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Re: ‘Magic mushroom’ enzyme mystery solved [Re: 24sevenZed] * 1
    #24554611 - 08/15/17 12:29 AM (3 years, 8 months ago)

it would also be a great high yielding culinary mushroom if it had the active part broken. It doesn't taste bad when prepared properly for cuisine.

with this breakthru give it a few years before you can have beer yeast make psilocybin/psilocin at home with a CRISPR kit or similar.


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OfflineAlan RockefellerM
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Nature Boy] * 1
    #24554636 - 08/15/17 12:46 AM (3 years, 8 months ago)

Quote:

24sevenZed said:
What I find more interesting about this is that it could allow one to develop knock out methods for these enzymes in, e.g. Psilocybe Cubensis, and to finally trade Cubensis (and other psilocybe) cultures legally.





And to sell them in grocery stores!  They are delicious cooked.

Quote:

Nature Boy said:
The line that caught my attention was the one that said "an enzyme that mediates two sequential amine methylation steps."  This infers that there is the potential for a wholly enzymatic synthesis of dimethyltryptamine (DMT).  Would love to read the paper that sets THAT process out in detail.  :super:




http://sci-hub.bz/10.1002/anie.201705489


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OfflineNature Boy
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Inspir3] * 1
    #24554845 - 08/15/17 03:21 AM (3 years, 8 months ago)

Quote:

Inspir3 said:
Quote:

Nature Boy said:
The line that caught my attention was the one that said "an enzyme that mediates two sequential amine methylation steps."  This infers that there is the potential for a wholly enzymatic synthesis of dimethyltryptamine (DMT).  Would love to read the paper that sets THAT process out in detail.  :super:



meaning it allows step 2 to go to step 4, skipping 3?




Geez. Ok, I'll spell it out. Start with tryptamine. Add enzyme.  Get  dimethyltryptamine (DMT).  Folks have been trying to find a way to encourage mushrooms to manufacture the related molecule DMT for years. Now there's apparently a synthetic enzymatic way to add two methyl groups to psilocybin which could quite possibly be extended to manufacture DMT in prodigious amounts without extracting from MHRB.  Remember, psilocybin is O-phosphoryl-4-OH-DMT!!!


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Edited by Nature Boy (08/15/17 03:29 AM)


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Offline24sevenZed
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Alan Rockefeller]
    #24554880 - 08/15/17 03:59 AM (3 years, 8 months ago)

Alan, thanks for the link. From the paper:

Quote:

Our results therefore imply that 2 (Psilocin) may not be a true substrate en route to 1 (Psilocybin). Given that PsiK readily turns over 2 (Psilocin) to 1 (Psilocybin), we propose that this activity represents a protective mechanism to rephosphorylate the instable 2 to the stable 1 in case of intracellular ester cleavage




Maybe I'm reading too much into that, but I find that to be nearly as interesting as the biosynthesis result itself. It suggests the evolutionary role of psilocybin is at least important enough for mushrooms to actually repair it as it breaks down.

I wonder if there are similar enzymes to repair, say, amatoxins, in poisonous species.


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OfflineWiiiiilson
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: 24sevenZed]
    #24555010 - 08/15/17 07:27 AM (3 years, 8 months ago)

Im sure there would be enzymes to repair other things like amatoxins. Such things probably exist in the fungal tissues as a deterrent or delirant to help prevent predation, or attract foraging organisms to help spread the spores and tissue - so the fungi has an evolutionary 'interest' in maintaining these metabolites.

An exciting prospect from this research is a PCR to detect these enzymes and give instant confirmation of active species vs non-actives. I've seen papers that use a PCR for a non coding satellite repeat region from psilocybe species to detect 'relatedness' - which correlated well with psychoactivity, but not a direct PCR for the enzymes responsible for psychoactive metabolite production.

I could whip up a set of PCR primers to detect these enzymes - it wouldn't be hard. You could then get genetic confirmation that something is active!

There are very likely to be homologues of these enzymes throughout the fungal kingdom with slightly different activity - perhaps ones with dual functions, or which modify different groups, or which modify the same groups with greater or lesser activity than these. This is exciting!


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OfflineAlan RockefellerM
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Wiiiiilson]
    #24555141 - 08/15/17 09:37 AM (3 years, 8 months ago)

Quote:

Wiiiiilson said:
An exciting prospect from this research is a PCR to detect these enzymes and give instant confirmation of active species vs non-actives. I've seen papers that use a PCR for a non coding satellite repeat region from psilocybe species to detect 'relatedness' - which correlated well with psychoactivity, but not a direct PCR for the enzymes responsible for psychoactive metabolite production.





Since the ability to produce psilocybin only evolved once and spread to various genera via horizontal gene transfer, that would be possible, and I intend to do it as soon as I get an anotated full genome sequence of an active species.    I don't think it would detect all actives though - it would just tell you if the DNA code to produce psilocybin was there.  I think many non-actives would also have this code in the genome, but deactivated do  to a small change somewhere else in the genome.  It still would be interesting to be able to screen for the presence of these genes with a simple PCR and electrophoresis assay.


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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Alan Rockefeller] * 2
    #24555234 - 08/15/17 10:34 AM (3 years, 8 months ago)

I say this is great, though the method starting from 4-acetoxyindole which is converted to 4-acetoxyindol-3-yl-N,N-dimethylglyoxylamide, which is then added dropwise to LAH in THF with stirring, and reflux is then maintained for a short time, then the mixture is cooled and the reaction is quenched with some water containing a small amount of THF. The reaction is then filtered under an inert atmosphere (N2), and the collected solids are washed, then the filtrate and lashings are combined and stripped of solvent, the resulting residue is then distilled, the solid distillate is then re-crystallized giving psilocin, while it has it's flaws and setbacks, really is not that bad.

Early synthesis of psilocin/psilocybin would use O-benzyl ether as a protecting group, which provides some further stability as far as intermediates, but also requires the extra step of reductive debenzylation, so, it would be 4-hydroxyindole to 4-benzyloxyindole through the sodium salt with benzoyl chloride, which is converted to 4-benzyloxyindole-3-glyoxylchloride with oxalyl chloride, the 4-benzyloxyindole-3-glyoxylchloride is then converted to  4-benzyloxy-3-(N,N-dimethyl-glyoxamide with dimethylamine. Then using LAH in dioxane 4-benzyloxy-N,N-dimethyltryptamine is produced brining us to the final step where the 4-benzyloxy-N,N-dimethyltryptamine is converted to 4-hydroxy-N,N-Dimethyltryptamine using hydrogen with a Pd catalyst on Al2O3.

Conversion to psilocybin from the last method only requires two additional steps, though there really does not seem to be much reason to do so.

Anyway, an enzymatic synthesis would be a bit more simple and could lead to larger scale production.

...

Someone asked about doing this with DMT...

the biosynthetic pathway for DMT starts with tryptophan which is decarboxylated (amino acid decarboxylase) to tryptamine, this tryptamine is then methylated by indole amine methyl transerase (INMT) in conjunction with S-Adenosyl methionine (SAM) (which is where the methyl group donation comes from), which becomes S-Adenosyl-L-homocysteine (SAH) as it donates the methyl group to the amine nitrogen of the tryptamine, giving N-methyl-tryptamine, which is again methylated by SAM in conjunction with INMT (the SAM becoming SAH as it donates the methyl group to the amine nitrogen of the N-methyl-tryptamine) giving N,N-Dimethyltryptamine.

In TIHKAL in the "DMT is everywhere" chapter shulgin mentions a hypothetical method for enzymatic synthesis of DMT
Shulgins method would use INMT and would work by constantly reconverting SAH to back to SAM, and then the SAM would constantly be becoming SAH as it donates methyl groups to tryptamine and N-Methyl-tryptamine, ultimately giving DMT...

Quote:

what a fabulous black box that would make. Get two enzyme preperations, one that can methylation s-adenosyl-homocysteine to S-adenosyl-methionine and another that can regenerate s-adenosyl-homocysteine by transferring a methyl group to the available amine. Two catalysts in a chamber heated to 37°c, with a spigot adding tryptamine at the top and another releasing DMT out the bottom. That's the science, I'll leave the details to the engineers.

-shulgin; TIHKAL; DMT is everywhere chapter





I did a pretty bad job here, too many distractions while writing all this, no motivation to edit it.


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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Alan Rockefeller] * 1
    #24555367 - 08/15/17 11:43 AM (3 years, 8 months ago)

Alan, I tried looking for the actual sequence but there is no accession listed in the paper and there are no full genomes for P. cubensis on Genbank yet, which is quite suspicious for a published paper. They dont even list any of the primers they used in the paper to make their clones. It makes me wonder how it passed review really - all we have is their word.

I was curious to know if this operon was on a mobile element - which is why I was searching for the sequence. Do you know if it actually is passed by HGT?
I didn't know that HGT was possible in higher fungi. Do they have plasmids and conjugative transposons too?

I suppose I should just google it, but Im interested to hear what you have to say.


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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Wiiiiilson] * 1
    #24555476 - 08/15/17 12:35 PM (3 years, 8 months ago)

Quote:

Wiiiiilson said:
Alan, I tried looking for the actual sequence but there is no accession listed in the paper and there are no full genomes for P. cubensis on Genbank yet, which is quite suspicious for a published paper. They dont even list any of the primers they used in the paper to make their clones. It makes me wonder how it passed review really - all we have is their word.




Some reviewers / journals require GenBank submissions, others do not.  I can't find it in GenBank either.



Quote:


I was curious to know if this operon was on a mobile element - which is why I was searching for the sequence. Do you know if it actually is passed by HGT?





This information comes from a talk at MSA a year ago.  The paper on that has not yet been published, and what is known about it is here:  https://www.shroomery.org/forums/showflat.php/Number/23524081


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Offlineorison319
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Re: ‘Magic mushroom’ enzyme mystery solved [Re: Alan Rockefeller]
    #24555551 - 08/15/17 01:13 PM (3 years, 8 months ago)

seen on reddit, didnt even bother to read it there. come here first. :awehigh:


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