Hello fellow organic redditors, I've been struggling with the synthesis of AdoDMNB cofator for a while now (SAH alkylation step), this cofactor is used in DNA alkylation and dealkylation (if you're feeling curious, you can read about Epigenetics, quite an interesting topic). If you have some free time, please read ahead, any ideas are appreciated!
The photo of this post: https://i.imgur.com/9P8vT9T.jpg
So the general idea of the reaction is SN2-type nucleophyllic attack of sulphur atom onto a carbon with a leaving group (the amino acid and the aromatic NH2 are protonated, because the reaction is carried out in acetic and formic (1:1) acid solution, hence the most nucleophyllic atom here is S). I've used a series of alkylating agents to produce this cofactor, yet none of the alkylating reagents seem to do the job (reaching only 15% or less conversion).
To make this post easier to comprehend, different alkylating agents are labeled as DMNB + the leaving group abbreviation (like Br, I, OAc, OTs and ONs). DMNB - 4,5-Dimethoxy-2-nitrobenzyl.
Firstly, I've tried DMNBBr and DMNBI (typically I'm using 6 eq. of alkylating reagents, so you can assume I'm using at least 6 eq. in any reaction) in addition to 6 eq. of silver acetate, which helps to polarize the C-Hal bond, making the carbon more electrophyllic, though the reaction slows down to a point where it doesn't proceed at all. In some literature scientists use silver triflate, still in the methods they list yield to be no more than 15%. All of these alkylating reactions were carried out in a mixture of 1:1 AcOH:Formic acid under argon gas.
Also I've tried the reaction with DMNBOAc, but it showed to be too weak of an electrophile (reaction proceeds, but extremely slow, so It's rendered useless in this reaction).
The next thing I've tried are aromatic sulfonates as leaving groups, including tosylate (DMNBOTs) and nosylate (DMNBONs), which on their own were quite a challenge to isolate. DMNBONs purified by column chromatography showed immediate equilibrium in solution with some 5 to 6 colorful, decaying after exposure to light compounds on TLC. The nosylate showed poor results in just the acid mixture (only trace amounts were detected by HPLC-MS), yet the addition of NH4OAc gave much better results (conversion was about 10-12%), but after some hours the reaction stopped completely. Using DMNBOTs showed similar results, not using NH4OAc the reaction went smoo
... keep reading on reddit ➡Taking SAMe daily for last 2 years, it reduced my depression and anxiety to comfortable levels. It also drastically helped my AS arthritis symptoms to a point where I get flair ups a few times a year (typically season changes) vs a few times a month. I am curious if anyone else has experienced positive effects like I have. I take 400mg enteric coated pills from Nature Made.
I received this L-Methionine product for free but I can't find any good evidence in support of why I should use it.
Reliable sources are scarce and it frequently is mistaken for SAMe.
Any help would be appreciated. Many thanks.
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