Next time you go to the library, search for books discussing the shikimic acid pathway and phenylpropanoid biosynthesis. But it will be a very hard topic if you don't have sufficient knowledge on both biology and biochemistry. But interesting nonetheless.
Will do. Actually I am way better at biology than chemistry, so it might be worth a shot. I never heard of shikimic acid, but it does seem to have a very interesting structure. A quick google search found this interesting link:
http://www.friedli.com/herbs/phytochem/shikimic.html (http://www.friedli.com/herbs/phytochem/shikimic.html)
In the reaction on the right, I wonder if it is the same enzyme that that removes the meta-hydroxy groups as adds the COCOOH. If not that would be 8) .
I wonder how many of these genes have been fully sequence and the appropriate primers for splicing into yeast found.
Surely its not as simple as inserting the gene, getting it expressed, and adding the appropriate precusor the the transgenic yeast, is it? Ohhh the things that could be done.... Indole-ethylamine n-methyltransferase here we come! (that has been expressed in yeast). Im sure the bees here have read these references, but just in case:
Michael A. Thompson Eunpyo Moon, Ung-Jin Kim, Jingping Xu, Michael J. Siciliano,
and Richard M. Weinshilboum, Human Indolethylamine N-Methyltransferase: cDNA Cloning and
Expression, Gene Cloning, and Chromosomal Localization, Genomics 61, 285–297 (1999)
and
Michael A. Thompson and Richard M. Weinshilboum, Rabbit Lung Indolethylamine N-Methyltransferase
cDNA AND GENE CLONING AND CHARACTERIZATION, THE JOURNAL OF BIOLOGICAL CHEMISTRY Vol. 273, No. 51, Issue of December 18, pp. 34502–34510, 1998
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000518259-shikimic.gif)
Brr, not so simple. Shikimic acid loses its 3- and 5-hydroxy groups very early. Yes, psycosmo, it`s not the same enzyme but you can see that enzymatic shikimic -> 3,4,5-trihydroxyphenylpyruvic appears to be imposible (or at least very hard ;) ).
I remembered epinephrine biosynthesis: tyrosine -> 3,4-dihydroxyphenylalanine -> dopamine -> norepinephrine -> adrenaline. Maybe mescaline will find its place somewhere here.
The chart is from http://www.genome.ad.jp (http://www.genome.ad.jp)
.
I remembered epinephrine biosynthesis: tyrosine -> 3,4-dihydroxyphenylalanine -> dopamine -> norepinephrine -> adrenaline. Maybe mescaline will find its place somewhere here.
From this link:
http://www.usm.maine.edu/~newton/Chy251_253/Lectures/AminesII/alkaloids.html (http://www.usm.maine.edu/~newton/Chy251_253/Lectures/AminesII/alkaloids.html)
It would seem that mescaline biosynth diverges from the more familar pathway you cite early on. The above link says that for mescaline, tyrosine is decarboxylated, then dopamine is produced by 3-hydroxylation (as opposed to dopa decarboxylase), then dopamine is methylated (presumably by Catechol-O-methyltransferase), and THEN the 5-hydroxylation occurs. So whatever enzyme does this is the one to be interested in.
It just seems so paradoxical from what little I know about chemistry because the 3-methoxy is is pushing the reaction to the 2-position via ortho-direction and the 6-position via para subsitution, and the alkylamino group is also pushing the reaction towards 2,6 subsitution. The 4-hydroxy is the only thing to push the reaction in favor the the 5-position. I could see steric hinderence preventing 2-hydroxylation, but not 6-hydroxylation.
So what enzyme is this, that can 5-hydroxylate 3-o-methyldopamine? If it has not yet been sequenced perhaps looking for genes homologous with tyrosine hydroxylase would be a good place to start?
And thanks for the cool diagram and link, thats one complicated set of pathways :o . How is it that reactions in nature can be at the same time so incredibly Rube Goldberg, but at the same time so delightfully elegant?
And if I might ask one other question, why are 3,5 hydroxys so vulnerable to removal? Is this a general rule, or only when there is a 1-carbonyl group? What conditions favor/disfavor 3,5 dehydroxylation?