Eddygp
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Chiral inversion of L-Theanine
This just in case: L-theanine is an aminoacid found in tea leaves.
I was wondering whether there was an easy pathway to perform a chiral inversion (maybe a Walden inversion if it is easy enough) on L-theanine, the
aminoacid. The properties of the natural L-theanine are very well-known, but D-theanine is virtually unknown and hasn't been subject to that much
research in comparison. Since the human body is chiral in nature (thalidomide... ... ...), I suspect that D-theanine would have quite different
properties from regular L-theanine, not only in chemical behaviour (diastereomers would be different) but also in how the body metabolises it and the
effects that it has in the human body.
there may be bugs in gfind
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Mesa
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I agree that it'd have different properties. It'd be biologically inactive.
Edit: Other than minor and inefficient competitor for L-theanine binding sites that is.
[Edited on 20-3-2015 by Mesa]
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Eddygp
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Quote: Originally posted by Mesa  | I agree that it'd have different properties. It'd be biologically inactive.
Edit: Other than minor and inefficient competitor for L-theanine binding sites that is.
[Edited on 20-3-2015 by Mesa] |
It might be biologically active, albeit in other ways (different from those of L-theanine). In fact, there is no way to know for sure beforehand.
Well. OK. There is one, but it is way too time-consuming.
there may be bugs in gfind
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Chemosynthesis
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Inter conversion of thalidomide at physiological conditions makes it kind of a nuanced example for chirality, despite still being used for some
disease treatments such as some cancers, inflammatory bowel disease, etc. Perhaps olfaction is more readily apparent and demonstrable.
Assuming purification to pharmaceutical standards, for simplicity maybe a Bamford-Stevens and then aminomercuration would do the trick. Resolve and
keep only your desired isomer. Clearly theoretical yield would start around 50% unless you had some fancy chiral auxiliary.
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