The synthesis of non natural amino acid 2-amino-3,3,4-trimethylpentanoic acid (Ipv), ready for solid phase peptide synthesis, has been developed. Copper(I) chloride Michael addn., followed by a Curtius rearrangement are the key steps for the Ipv synthesis. The racemic valine/leucine chimeric amino acid was then successfully inserted in position 5 of neuropeptide S (NPS) and the diastereomeric mixt. sepd. by reverse phase HPLC. The two diastereomeric NPS derivs. were tested for intracellular calcium mobilization using HEK293 cells stably expressing the mouse NPS receptor where they behaved as partial agonist and pure antagonist.
Racemic synthesis and solid phase peptide synthesis application of the chimeric Valine/Leucine derivative 2-amino-3,3,4-trimethyl-pentanoic acid / M., Pelà; L., Del Zoppo; L., Allegri; E., Marzola; C., Trapella; C., Ruzza; G., Calo???; Perissutti, Elisa; Frecentese, Francesco; S., Salvadori; R., Guerrini. - In: PHARMAZIE. - ISSN 0031-7144. - 68:7(2014), pp. 496-499. [10.1691/ph.2014.3961]
Racemic synthesis and solid phase peptide synthesis application of the chimeric Valine/Leucine derivative 2-amino-3,3,4-trimethyl-pentanoic acid
PERISSUTTI, ELISA;FRECENTESE, FRANCESCO;
2014
Abstract
The synthesis of non natural amino acid 2-amino-3,3,4-trimethylpentanoic acid (Ipv), ready for solid phase peptide synthesis, has been developed. Copper(I) chloride Michael addn., followed by a Curtius rearrangement are the key steps for the Ipv synthesis. The racemic valine/leucine chimeric amino acid was then successfully inserted in position 5 of neuropeptide S (NPS) and the diastereomeric mixt. sepd. by reverse phase HPLC. The two diastereomeric NPS derivs. were tested for intracellular calcium mobilization using HEK293 cells stably expressing the mouse NPS receptor where they behaved as partial agonist and pure antagonist.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
