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Author: Subject: N-Methyl-d,l Alanine
phlogiston
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[*] posted on 6-6-2013 at 07:50


I don't think I have a real reference for that method. I just improvised it based on a single line in a paper. I don't remember the paper in detail but I do recall it did not provide a detailed experimental procedure for that. but I'll have a look if I can find that paper again.

I actually do chiral separation by LC almost daily because my research work revolves around the functions and metabolism of D-amino acids in humans (yes, in contrast to what most textbooks will tell you we do make and use D-amino acids, as neurotransmitters and for regulation of certain hormones).

I devised a method which is based on derivatisation with an enantiomerically pure reagent. I can then separate the derivatised enantiomers (which are diastereoisomers) of the different amino acids on a simple non-chiral C18 UPLC column (UPLC=essentially just HPLC but with even smaller particles/higher pressures).
For preparative purposes, it would probably be easier to use a chiral column (or you would have to undo the derivatisation somehow). Alternatively, you can sometimes degrade/remove the L-enantiomer enzymatically to obtain pure D-enantiomer.

However, all this may be a bit difficult in an amateur setting. chiral HPLC columns, purified enzymes etc are probably not easy to acquire.




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[*] posted on 6-6-2013 at 13:47


Waffles, try tartaric acid or naproxen (tartaric acid first) and get the hang of that.



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Waffles SS
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[*] posted on 7-6-2013 at 08:17


I think resolution of amino acids by tartaric acid is not possible
Quote:

Vogel Practical Organic Chemistry 5th, P.815
Untitled-2.jpg - 366kB

This method should be effective for resolution of N-methyl Alanine too.am i wrong?
@phlogiston,
This is possible to use Chiral Column chromatography for resolution of Amino Acids?(not HPLC )


[Edited on 7-6-2013 by Waffles SS]
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[*] posted on 11-7-2013 at 00:33


I can do the original method to make n=methylalanine but how do I get it out of the solution ? ? ? ? ? ? ?



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[*] posted on 11-7-2013 at 03:56


For amino acids, I have only used HPLC-based methods, but in principle I don't see any reason why it could not be done.

There are stationary chiral phases available for this kind of work. See for instance:

Preparative chiral chromatographic resolution of enantiomers in drug discovery
Journal of Biochemical and Biophysical Methods
Volume 54, Issues 1–3, 31 December 2002, Pages 11–23

I'd be happy to mail you the pdf if you can't get it without a subscription.




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