N-Fmoc-protected(alpha-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation

Chemical Biology & Drug Design
Alan R KatritzkyNiveen M Khashab

Abstract

N-Fmoc-protected(alpha-aminoacyl)benzotriazoles 1a-d readily afford chiral N-Fmoc-protected-alpha-dipeptides 2a-f (77-89%). Compounds 2a-f are further converted into N-Fmoc-protected(alpha-dipeptidoyl)benzotriazoles 3a-f (71% average yield). Under mild microwave irradiation, 3a-f are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).

References

Feb 1, 1994·International Journal of Peptide and Protein Research·N U ObeyesekereJ S McMurray
Apr 1, 1993·International Journal of Peptide and Protein Research·H MiharaT Fujimoto
Oct 20, 2001·Bioorganicheskaia khimiia·S V KolobanovaV M Stepanov
Jun 14, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Spyros GoulasKleomenis Barlos
Dec 21, 2006·Chemical Biology & Drug Design·Alan R KatritzkyParul Angrish
Oct 24, 2007·Chemical Biology & Drug Design·Alan R KatritzkyCarrie Haskell-Luevano

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Citations

Jul 29, 2009·Chemical Biology & Drug Design·Alan R KatritzkySrinivasa R Tala
Mar 16, 2013·Journal of Peptide Science : an Official Publication of the European Peptide Society·G Verardo, A Gorassini
Apr 2, 2011·The Journal of Organic Chemistry·Ilker AvanAlan R Katritzky
Aug 27, 2011·Chemical Reviews·Ayman El-Faham, Fernando Albericio
Oct 16, 2009·Organic & Biomolecular Chemistry·Alan Roy KatritzkyZakaria Kamel Abdel-Samii
Jul 9, 2021·European Journal of Medicinal Chemistry·Lima RodriguesMahesh S Majik

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