I am trying to couple an aromatic spacer in a peptide. The problem is that the coupling barely happens and the coupling of the next amino acid almost never happens. I use fmoc strategy, and the coupling agents are DIC and HObt, what other coupling agents or methods that can allow me to couple PABA into the middle of the sequence.
Dear Mo'ad,
our group synthesized the PABA-containing natural product albicidin using BTC as a coupling agent. Have a look at the supplemental of this paper:
Article Total Synthesis of Albicidin: A Lead Structure from Xanthomo...
Maybe this is something you could try. Good luck with your synthesis!
Kind regards,
Lorin
In my experience, HATU is usually my go-to for difficult couplings (with base like DIPEA). This is particularly useful in peptide synthesis because there is reportedly less risk for epimerization of your C-terminus peptide chiral center.
https://en.wikipedia.org/wiki/HATU
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