Solid-phase synthesis of cyclic polyamines

Application of N-Dodecyl l-Peptide to Enhance Serum Stability while Maintaining Inhibitory Effects on Myometrial Contractions Ex Vivo

“…With the o NBS group installed, sulfonamide resin 5 was treated with di- iso -propyl azodicarboxylate (DIAD), triphenylphosphine and farnesol. N -Farnesyl peptide resin 6 was provided in 55% conversion as demonstrated by LC-MS analysis of material after resin cleavage [50,51,52,53]. The o NBS group was removed by treatment with thiophenol and DBU in DMF [52].…”

Mitsunobu Reaction on Solid Support for Peptide N-terminal Farnesylation

“…After removal of the N-terminal Fmoc protection, an para-nitrosulfonyl (Nosyl) group was installed by treating the resin-bound peptide with nosyl chloride and di-isopropylethylamine in DMF [9,10]. The Mitsunobu reaction was performed using farnesol, diethylazodicarboxylate and triphenylphosphine in THF to install the farnesyl chain.…”

Regioselective solid-phase synthesis of N-mono-hydroxylated and N-mono-methylated acylpolyamine spider toxins using an 2-(ortho-nitrophenyl)ethanal-modified resin

“…The initially used classical synthetic approaches to obtain spider toxins by in-solution chemistry proved feasible, 15 but they have been progressively replaced by methods of solid phase chemistry. [6][7][8][9][10][11][12][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] Such methods proved to be more flexible and more efficient. In particular, laborious work-up and purification procedures with the usually rather polar synthetic intermediates could be avoided.…”