[ronholes7059]

Also, wanted to post and update on the reaction I did yesterday.

So I set 4 reactions, with varying amounts of DMP and keeping the 3-chloro-1,2-propane-diol amount the same.  I added 0 (control), 2, 4, and 6 molar equivalents of DMP. I then added CH2Cl2 up to the same amount in each vial. Interestingly, immediately upon addition of DMP there was a precipitate formed in the 2 eq tube, and slight cloudiness to tubes with 4, and 6 eq.  After 4 hours all tubes were clear except the tube with 2 eq.  I spotted each on TLC after 4 hours (but haven't runt hem yet, not in the lab today) and let them go, will check them tomorrow and spot TLC again.  I will do a general stain and a DNP staining that is for carbonyls. 

I'll update tomorrow but thought it was interesting that the more DMP was added, the less precipitate was formed. 

[orgopete]

I understand that the listing of 3-chloro-2-oxopropanal may have been for a custom synthesis, but it does have a CAS RegNo. I think that means there is a literature description of its synthesis. Might that be another place to start or at least learn more about that compound?

[Dan]

So I am trying to make an analogue to methylglyoxal (MG), which is the same structure except a H replacing the Azido group.  I know MG exists in equilibrium in three forms, the dicarboyl, the mono-hydrate and di-hydrate.

So we are interested in MG modifications of proteins and analyzing them by MS, we do a lot of proteomics work on our lab, so I wanted to try and come up with an analogue that we could treat the cells/animals with then pull out the mods using click chemistry. 

I don't know a lot about these protein modifications, but from what I gather it seems as though you could have a longer carbon chain between the α-ketoaldehyde and the azide click handle. Something like this:



Shifting the azide one carbon further away from the ketone should improve stability because enolisation will be less favourable than for 3-azidopyruvaldehyde. The spacer could even be longer, which might make the azide more accessible for subsequent click reactions.