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soma
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[*] posted on 30-6-2017 at 02:52
difference between NAC ester and NAC amide

It is recommended that n-acetyl cysteine amide be stored at below 0C temps. I assume that's because it dimerizes easily. I'm wondering if n-acetyl cysteine ethyl ester would be as susceptible.

I haven't been able to find much information on the ester. Aldrich has the methyl ester but not much info (that I could find).
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[*] posted on 30-6-2017 at 13:21


Probably. The dimerization is oxidative. Cold and preferably under nitrogen or argon would slow or stop the degradation.
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[*] posted on 30-6-2017 at 13:50


An only slightly related question- can the thiol group of cysteine be oxidized to a sulphonic acid?



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[*] posted on 30-6-2017 at 13:54


Yes. The resulting sulfonic acid is known as cysteic acid. Many common oxidizing agents (most notably peroxyacids) will do it.

[Edited on 6-30-2017 by Metacelsus]



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[*] posted on 30-6-2017 at 15:18


If you're interested in cysteic acid as an intermediate in some synthesis, there's a good chance that taurine could save you the effort as an entry point unless you need the COOH functionality.
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[*] posted on 1-7-2017 at 02:09


I'm wondering how esterification or ammonolysis of n-acetyl cysteine would effect the pH and water solubility.

Also wondering how quickly the dimer forms at higher pH and how quickly it splits at lower pH.



[Edited on 2-7-2017 by soma]
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