Syntheses of Chiral N‐(Protected) Tri‐ and Tetrapeptide Conjugates

Abstract

Cbz-(protected)-tri-and tetrapeptide conjugates with steroids, sugars, terpenes, and heterocycles were prepared using Cbz-(protected)-tri-and tetrapeptidoylbenzotriazoles as active intermediates.

Synthesis and Antimalarial Bioassay of Quinine – Peptide Conjugates

“…The Cbz‐protected tripeptide 10 was synthesized in 80% yield by our reported method of stepwise coupling of amino acids with subsequent benzotriazole‐activated N ‐protected amino acid analog 9d in solution phase. Compound 10 was activated by benzotriazole to obtain 11 in 72% yields (Scheme ).…”

“…We prepared amino acid and peptide conjugates of quinine 12a-n by O-acylation of quinine 1 with N-protected acylbenzotriazoles 9 in the presence of K 2 CO 3 in anhydrous DMF under microwave irradiation (50°C, 20 W) for 10-30 min (Scheme 5, Table 1). Compounds 12a-n were purified by column chromatography and characterized by 1 H NMR, 13 C NMR, and HRMS analysis.…”

“…Experimental details for compounds 2-11. 1 H, 13 C and CHN/HRMS spectra for 4f, 4g, 7e, 7f, 9b, 9c, 11 and 12a-n and graphs for antimalarial bioassay of 12a-n and quinine. This material is available free.…”

“…664.3017, found 664.3035. (2S)-((1R)-(6-Methoxyquinolin-4-yl)(8vinylquinuclidin-2-yl)methyl) 2-(benzylamino)-3-(benzylthio)propanoate (Z-L-Cys(Bz)-QN, 12j) Oil (65%); 1 H NMR (CDCl 3 ) d 8.74-8.68 (m, 1H), 8.02-7.97 (m, 1H), 7.37-7.14 (m, 15H), 6.52-6.42 (m, 1H), 5.86-5.75 (m, 1H), 5.49-4.45 (m, 1H), 5.12-4.99 (m, 4H), 4.65-4.58 (m, 1H), 3.93 (s, 3H), 3.64-3.53 (m, 1H), 3.38-3.29 (m, 1H), 3.08-2.62 (m, 4H), 2.27-1.46 (m, 7H);13 C NMR (CDCl 3 ) d 174.8, 162.7, 160.5, 152.1, 149.3, 147.3, 146.3, 142.0, 140.7, 136.5, 134.1, 133.6, 133.3, 133.0, 132.0, 131.6, 126.6, 123.6, 119.3, 106.0, 80.0, 71.9, 70.6, 63.8, 61.3, 60.3, 58.2, 47.1, 44.2, 41.2, 37.8, 32.1, 20.0. HRMS m/z for C 37 H 41 N 3 O 3 S [M + H] + calcd.…”

Synthesis, molecular docking and anticancer studies of peptides and iso-peptides

“…[13][14][15][16] Since then tremendous progress has been achieved in this field. 17 This solution phase benzotriazole mediated peptide coupling avoids both epimerization and hydrolysis due to fast coupling rate.…”