I would like to make short oligopeptides with aldehyde side chains. My first thought is oxidation of oligo-homoserine peptides (Fmoc-L-Hse(Trt)-OH is commercially available, and therefore very convenient). Any thoughts or alternative approaches? I've seen a couple of relatively old papers describing the synthesis of aldehyde building blocks (i.e. Tetrahedron Letters 2002, 43, 2303–2306), but not much has been done with them later. Thanks.
Crazy idea, but: what about using an iminoacid (such as P5C)? The protocol would be: hydrolysis of P5C, aldehyde protection, and coupling.
Creation of the aldehyde from homoserine sounds okay, just be careful not to over oxidize. I'm not sure of the reaction pathway (energetically); it might be the case that the aldehyde is difficult to form, then it is quickly consumed and over oxidizes to the acid.
You'll have to protect the aldehyde group to use it for peptide synthesis. Dehydration of 1,2-ethanediol will give you an acetal that should be appropriate for Fmoc-base synthesis. Global deprotection at an acid pH will release the acetal to reform the aldehyde.
Hope this helps
Thanks for the input everyone. Charles, yes, the diol is a good option an indeed it's what they use in the building block approach I mentioned. Thanks
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