The Hive > Tryptamine Chemistry
Enzyme Sequences
Xenonpill:
These are from The Resonance Project v2.15 winter 97/98.
Some of the article is available on the resonance project's website.
Tryptophan Hydroxylase:
Amino Acids: F,S,Q,E,I,G,L,A
Nucleuotides (human, rat, rabbit, mouse): TTC,TCC,CAA,GAA,ATT,GGC,CTG,GCT
Tryptophan Decarboxylase:
Amino Acids: G,K,E,M,V,D,Y
Nucleotides:
Human: GGG,AAG,GAG,ATG,GTG,GAT,TAC
Cow: GGG,AAG,GAG,ATG,GTG,GAT,TAC
Rat: GGG,AAG,GAG,ATG,GTG,GAT,TAT
Hydroxyindole O-Methyltransferase:
Amino Acids: D,A,V,R,E,G,R,N
Nucleotides:
Human: GAC,GCC,GTG,AGA,GAA,GGA,AGG,AAC
Chicken: GAT,GCT,GTG,AGA,GAA,GGA,AGA,AAT
Unfortunatly, no references were supplied in the print article or at www.resproject.com, however, it may be possible to get the refs by bugging someone at the resonance project.
KrZ, would this kind of thing help you make a yeast that produces gobs of DMT when mixed with water?
Xenonpill
KrZ:
Tryptophan->Tryptamine
DEFINITION C.roseus tdc gene for tryptophan decarboxylase.
ACCESSION X67662
/translation="MGSIDSTNVAMSNSPVGEFKPLEAEEFRKQAHRMVDFIADYYKN VETYPVLSEVEPGYLRKRIPETAPYLPEPLDDIMKDIQKDIIPGMTNWMSPNFYAFFP ATVSSAAFLGEMLSTALNSVGFTWVSSPAATELEMIVMDWLAQILKLPKSFMFSGTGG GVIQNTTSESILCTIIAARERALEKLGPDSIGKLVCYGSDQTHTMFPKTCKLAGIYPN NIRLIPTTVETDFGISPQVLRKMVEDDVAAGYVPLFLCATLGTTSTTATDPVDSLSEI ANEFGIWIHVDAAYAGSACICPEFRHYLDGIERVDSLSLSPHKWLLAYLDCTCLWVKQ PHLLLRALTTNPEYLKNKQSDLDKVVDFKNWQIATGRKFRSLKLWLILRSYGVVNLQS HIRSDVAMGKMFEEWVRSDSRFEIVVPRNFSLVCFRLKPDVSSLHVEEVNKKLLDMLN STGRVYMTHTIVGGIYMLRLAVGSSLTEEHHVRRVWDLIQKLTDDLLKEA"
DEFINITION Oryctolagus cuniculus indolethylamine N-methyltransferase (INMT) mRNA, complete cds.
ACCESSION AF077826
/translation="MEGGFTGGDEYQKHFLPRDYLNTYYSFQSGPSPEAEMLKFNLEC LHKTFGPGGLQGDTLIDIGSGPTIYQVLAACESFKDITLSDFTDRNREELAKWLKKEP GAYDWTPALKFACELEGNSGRWQEKAEKLRATVKRVLKCDANLSNPLTPVVLPPADCV LTLLAMECACCSLDAYRAALRNLASLLKPGGHLVTTVTLQLSSYMVGEREFSCVALEK EEVEQAVLDAGFDIEQLLYSPQSYSASTAPNRGVCFLVARKKPGS"
This can also catalyze the second methylation according to quicksilver (who has been alot of help, and I am very appreciative of).
Complete mRNAs for every step, nothing too gigantic either...
Quicksilver:
KrZ-
Go ahead and post my last PM if you still have it. Maybe there are enough bees with molec' bio' background to find that last step that I couldn't.
Basically my work ended in an e.coli that produces DMT (not psilocin) because there is no cloned enzyme that will hydroxylate the 4 position on DMT. (and thus convert DMT->psilocin) Not a total loss, but not what we were looking for.
Xenopill-
If you know of a indole-hydroxylase, or tryptamine hydroxylase that will work, you'll make me a happy bee.
KrZ, thanks for the acknowledgement. In doing so, it reaffirms what most of us know about your strength of character already.
-quicksilver-
Rhodium:
Quicksilver: Are yuo telling me that there already exist a bacterium which can convert tryptophan to DMT? How many millimoles can a culture churn out per hour?
http://rhodium.lycaeum.org
KrZ:
KrZ-
I wasn't able to get any of the articles, but I'm not sure of their worth anyway. (since they all pre-date molecular bio/DNA techniques)
Ironically, the textbook Biochemistry by Mathews/vanHolde Chapter 21 page 740, review question 4, actually asks for a biosynthesis of
psilocybin from tryptophan. Too bad there's no answers in the book.....
Regardless, you stated:
Tryptophan -1-> Tryptamine -2-> N-Methyl-tryptamine -3-> N,N-dimethyltryptamine -4-> psilocin -5-> psilocybin
The enzymes for the first 3 steps are known, and the protein+DNA sequences are known too.
1-Tryptophan->Tryptamine
Enzyme=aromatic amino acid decarboxylase
AKA: AAAD, AKA: dopadecarboxylase
Genbank Accession# M88700 (protein sequence=AAA20894)
Reference:Human dopa decarboxylase: localization to human chromosome 7p11 and characterization of hepatic cDNAs. Genomics 13
(2), 469-471 (1992)
2-Tryptamine -> N-Methyl-tryptamine
Enzyme=Indolethylamine-N-Methyltransferase
AKA INMT
Genebank Accession# NM_006774
Reference:Human indolethylamine N-methyltransferase: cDNA cloning and expression, gene cloning, and chromosomal localization.
Genomics 61 (3), 285-297 (1999)
3-N-Methyl-tryptamine -> N,N-DiMethyl-tryptamine
Same as #2
4-N,N-dimethyltryptamine -> psilocin
There most likely isn't a human gene for this. (otherwise we'd all be alot happier people)
I find no references in medline for: indole-hydroxylase, trptamine-hydoxylase, or indolamine-hydroxylase, leading me to believe
there is no human (or other species) homolog. Dead end? My first thoughts are maybe the psilocin step is impossible at this time, or
at least until someone clones the gene responsible. So where from here? Perhaps the 5-hydroxyderivative would be more attainable.
See 5-OH-N,N-DMT http://www.erowid.org/library/books_online/tihkal/tihkal19.shtml
Shulgin is less than enthusiastic about this compound.
This could be accomplished with tryptophan hydroxylase. Worth the effort?? I'm skeptical.
5-psilocin -> psilocybin
Haven't looked yet.
That's all my ramblings. Any feedback would be much appreciated.
Cheers.
-quicksilver-
In reply to:
1. Agurell, S., Blomkvist,S. and Catalfomo, P.. "Biosynthesis of Psilocybin in Submerged Culture of Psilocybin cubensis: Part I.
Incorporation of labeled tryptophan and tryptamine," Acta Pharm. Suecica, Vol. 3 (1966), 37-44.
2. Agurell, S., Lars, J. and and Nilsson, C.. "Biosynthesis of Psilocybin: Part II. Incorporation of Labelled Tryptamine Derivatives, Acta
Chemica Scandinavica, Vol. 22, No. 4 (1968), 1210-1218.
6. Catalfomo, P. and Tyler, V. E., Jr.. "The Production of Psilocybin in Submerged Culture by Psilocybe cubensis, Lloydia, Vol. 27, No.l
(March 11. Leung, A.Y. and Paul, A.G.. "The Relationship of Carbon and Nitrogen Nutrition of Psilocybe baecocystis to the Production of
Psilocybin and its Analogs," Lloydia, Vol. 32, No. 1(March, 1969), 66-71.1964), 53-63.
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