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ESI of protected Arginine peptide

Posted: Mon Sep 14, 2009 8:23 pm
by xinshou
dear All

I have a peptide of which the only residues are Arginie (7 total ) and Glycine (2 total). The side chains of the Arginine (guanidine) was protected by pbf.

I need to do some modifications to this peptide and plan to use ESI to monitor the reaction progress. As the peptide is not dissolved in water. I am using DMF (dimethylforamide) as solvent.

When I tried to measure ESI, I diluted the peptide/DMF solution 10 times using water, and injected into ESI. However I could not see any expected peaks.

My question is: can I use ESI to detect this peptide ? As the side chains of the Arginine was protected by pbf, is the peptide ionizable under ESI condition? Does DMF do anything bad to the ESI?

Posted: Mon Sep 14, 2009 9:43 pm
by sam.pedraglio
Are you sure your protecting groups are not "ESI labile"?
Excuse me the stupid question but I'm not familiar with this chemistry.

Posted: Tue Sep 15, 2009 4:06 pm
by xinshou
Here is the structure of protected Arginine residue:

Image


Please help!

Posted: Wed Sep 16, 2009 4:28 pm
by sam.pedraglio
In my opinion you shouldn't have any problem detecting your peptide.
Two questions:
1) are you doing an injection or a lc analysis?
2) What do you mean with "Expected peaks"? Are you talking about fragments or charge state?