Copper-catalyzed N-arylation of semicarbazones for the synthesis of aza-arylglycine-containing aza-peptides.
Organic letters
confidence
Key findings
Chemical synthesis of aza-arylglycine peptides based on GHRP-6 via copper-catalyzed N-arylation of semicarbazone; CD spectroscopy showed beta-turn propensity.
View source on PubMed (PMID 20536163) ↗
- Sample size
- 13 aza-arylglycine peptides
- Population
- Not applicable (chemical synthesis study)
- Dosing
- Not applicable
- Duration
- Not reported
- Route
- Not applicable
- Blinding
- not_reported
- Controls
- none
- Drug class
- OTC organ bioregulator
Full abstract
Parallel synthesis of 13 aza-arylglycine peptides, based on the hexapeptide sequence of Growth Hormone Releasing Peptide-6 (GHRP-6), was accomplished via selective N-arylation of a semicarbazone peptide building block anchored on Rink amide resin. Aza-peptides possessing aza-indolylglycine and aza-imidazoylglycine residues were obtained through use of the corresponding heteroaryl iodides, yielding, respectively, aza-Trp and aza-His peptidomimics. CD spectroscopy indicated the propensity for aza-peptides, containing aza-arylglycines at the Trp(4) position of the GHRP-6 sequence, to adopt beta-turns.