I am incorporating di/tripeptides into an anhydrous reaction carried out in either DMF or DMSO but have encountered solubility issues with the peptides I have used so far, being far more water-soluble. Which amino acids typically confer high solubility in either of these solvents?
Hi Leigh
I think this article will help. Article Dipeptide-Catalyzed Asymmetric Aldol Condensation of Acetone...
Hi Leigh-Anne Gavin
I would think that peptides bearing aromatic and non-polar side chains are more DMF/DMSO soluble (watch out! Gly, and even Ala, are another worlds ;-) ). Peptides bearing amino acids with polar side chains (Arg, Lys, Asp, Glu) might be more water-soluble, especially if they come as salts/zwitterions. If it does not interfere with your reaction, maybe adding some uL of TFA might be of great help.
Good luck!
Of course, the hydrophilic residues containing AA (Amino Acid) will render more aqueous solubility, but the aqueous solubility is not restricting only to this. The zwitterionic format, and also dependent upon the temperature of solvation, intermolecular forces, H-bondings, rate of solubilization, etc. There are more solvents used for solubilizing peptides of this which includes THF, 1,4-Dioxane, in addition to DMF and DMSO. The nature of solvent is also important, protic or protogenic solvents will be helpful.
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