Coupling reagents resembling the structure of Merrifield resin were designed and prepared from 2-chloro-4,6-dibenzyloxy-1,3,5-triazine and the different tertiary bases N-methylmorpholine, N-methylpiperidine, and DABCO. As previously observed for DMTMM, the appropriate N-(4,6-dibenzyloxy-1,3,5-triazin-2-yl) ammonium chloride salts were not suitable as efficient coupling reagents because of their low stability. On the other hand, the stability of the N-(4,6-dibenzyloxy-1,3,5-triazin-2-yl) ammonium tetrafluoroborates was suitable enough for prolonged storage and convenient application in SPPS. Moreover, we observed that the superactive intermediates formed during activation of Fmoc–Aib–OH with 4,6-dibenzyloxy- 1,3,5-triazine-based coupling reagents lead to an increase in its concentration inside the polystyrene resin. Therefore, we hypothesize that this increase can enhance efficiency of 4,6- dibenzyloxy-1,3,5-triazine-based coupling reagents in SPPS.

Benzyloxy derivatives of triazine-based coupling reagents designed for an efficient solid phase peptide synthesis on polystyrene resin / K. JASTRZABEK; B. KOLESINSKA; G. SABATINO; F. RIZZOLO; A.M. PAPINI; Z.J. KAMINSKI. - In: INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS. - ISSN 1573-3149. - STAMPA. - 13:(2007), pp. 229-236. [10.1007/s10989-006-9071-y]

Benzyloxy derivatives of triazine-based coupling reagents designed for an efficient solid phase peptide synthesis on polystyrene resin.

B. KOLESINSKA;SABATINO, GIUSEPPINA;F. RIZZOLO;PAPINI, ANNA MARIA;
2007

Abstract

Coupling reagents resembling the structure of Merrifield resin were designed and prepared from 2-chloro-4,6-dibenzyloxy-1,3,5-triazine and the different tertiary bases N-methylmorpholine, N-methylpiperidine, and DABCO. As previously observed for DMTMM, the appropriate N-(4,6-dibenzyloxy-1,3,5-triazin-2-yl) ammonium chloride salts were not suitable as efficient coupling reagents because of their low stability. On the other hand, the stability of the N-(4,6-dibenzyloxy-1,3,5-triazin-2-yl) ammonium tetrafluoroborates was suitable enough for prolonged storage and convenient application in SPPS. Moreover, we observed that the superactive intermediates formed during activation of Fmoc–Aib–OH with 4,6-dibenzyloxy- 1,3,5-triazine-based coupling reagents lead to an increase in its concentration inside the polystyrene resin. Therefore, we hypothesize that this increase can enhance efficiency of 4,6- dibenzyloxy-1,3,5-triazine-based coupling reagents in SPPS.
2007
13
229
236
K. JASTRZABEK; B. KOLESINSKA; G. SABATINO; F. RIZZOLO; A.M. PAPINI; Z.J. KAMINSKI
File in questo prodotto:
File Dimensione Formato  
IntJPeptResTher_2007(1-2)_229-236(DibenzyloxyKaminski).pdf

Accesso chiuso

Tipologia: Altro
Licenza: Tutti i diritti riservati
Dimensione 281.55 kB
Formato Adobe PDF
281.55 kB Adobe PDF   Richiedi una copia

I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/219629
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 14
social impact