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Author: Subject: Yeast in organic synthesis
frogfot
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[*] posted on 27-5-2004 at 10:17
Yeast in organic synthesis


There was some thread that gave an adress to an e-book about this, but I couldn't download it..

Anyway, do anyone have some interesting and simple reactions that could be carried out with help of yeast?
As I understand, yeast can reduce carbonyl and nitro groups (not sure on second one).

In org chem we did reduction of.. I think it was acetoacetate. That was a tedious lab since separation was made by a solvent, alot of solvent :o
I wanna test some similar reaction with more widely available precursor(s) where product is preferrably removed by destillation (but it doesn't matter really). Any example would be nice to hear.. maby someone have experience in such synthesises.

Btw, www.orgsyn.org have some references to reactions with yeast but precursors seems to be a bit complex..

Oh, and ethanole brewing is already tested :D

..maby reducing mesityl oxide..
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[*] posted on 30-5-2004 at 01:32


I'm interested in what yeast can be made to do, but so far everything Ive read follows the same pattern. Enzymes do very specific jobs usually only on one target molecule, so the bacteria that turn wine into vinigar for example, we wouldnt expect to work with methyl alcohol unless it had specific additional enzymes for the job.

In the same way all the products I know about are part of an existing cycle.

Glycerol, Butyric acid, Lactic acid, Ethanol, Succinic acid etc are all normally present, and the key is just to cripple part of the cycle so one chemical accumulates in high yeild.

If theres any information that yeast will reduce carboyl functions generally, or nitro groups generally, Id be interested to see it, but so far everything Ive seen fits the same enzyme pattern of one enzyme for one specific reaction.
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frogfot
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[*] posted on 3-6-2004 at 09:32


Oh, sorry I'm a bit late.. but today school ended :P

I just made an assumption that it reduces carbonyl groups... In this file:

http://bio.bio.unibuc.ro/biochemistry/Enzimology/Vol6No4-200...

they mentioned that the more nonsymmetric ketones are the better in enantioselectivity, that is, with one large, and one small side like Ph-CO-Me it'll produce more L-product. Thats about all info I could google..

Heres some info on nitro group reduction:
http://www.ch.ic.ac.uk/ectoc/papers/04/4-Oxidoreductases.htm...

[Edited on 3-6-2004 by frogfot]

[Edited on 3-6-2004 by frogfot]
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Organikum
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[*] posted on 3-6-2004 at 10:19


There is a file on the ftp called "bakers yeast in organic synthesis", there are several books on the ftp covering this - I am not sure what you need more.
:P




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[*] posted on 3-6-2004 at 16:23


Frogfot, interesting sites :)

Principally, most, if not all reactions can be theoretically done with enzymes. EXcept maybe some highly endothermic ones. I dont necessarily mean natural enzymes, but rather designed ones.

Anyway- regarding the reactions Marvin is speaking of - there are some enzymes that perform a general reaction, such as nitro group reductions, or there are enzymes that are specific to a particular reaction with a particular compound. To use normal bakers yeast to use one of these enzymes specifically is probably rather inefficient - except for the traditional ones (--> ethanol production).
Instead, what is done today (AND employed industrially) is to over-express those enzymes that are necessary for a given reaction, thereby enhancing reaction rates - or, more commonly, to overexpress it, and toisolate the enzymes, and perform the reactions in vitro (in reaction vessels, aka in the test tube).
This is done, for instance, for the production of many antibiotics (particularly chiral ones).
Here the necessary enzymes are covalently linked to beads (often glass, or plastics), and incubated with the antibiotic precursor. Once the reaction is complete, the product is flushed through, and the enzyme beads are recovered. A great technique, with very little chemical waste and recyclable catalyst! Unfortunately, not particularly easy to do for the home chemist :(

PS shouldnt this go into the biochem section?

[Edited on 4-6-2004 by chemoleo]




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[*] posted on 4-6-2004 at 00:13


Orgy, on what ftp? Just got access to axehandles ftp, there seems to be quite alot on enzymes, but I can't find that book (title sounds very interesting). :)

The problem is, I dunno much biochemistry to properly affect the metabolism (citric acid cycle and so on) of yeast.. to accumulate specific involved compounds.

There is some info on sucrose to acetone at high pH and/or addition of sodium sulfide. Though I dont have the specifics..

Mmm.. industrial biocatalysts.. how about a column of yeast for continious brew making.. in school we made small yeast balls, I don't remember how but there was some binder added to yeast, and this mass was dropped into stirred water (the drops remained undissolved), and the binder solidifyed making uniform balls. That would be tedious brewing..

Oh, soz, I couldn't decide where to put this thread.. title kinda belongs in both sections.. :P

[Edited on 4-6-2004 by frogfot]
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[*] posted on 4-6-2004 at 04:13


look harder.

bakers_yeast_org_synth.pdf
is the exact name.

Also of interest:
biocatalysis_book.rar




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[*] posted on 15-6-2004 at 10:20


have a look on the hive in the serious chemistry forum. Theres a superb thread on biosynthesis using yeast to produce some interesting compounds. I wont supply the link as I think you have to be a registered member to view the Serious chem forum and novel discourse forums.
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