ChemInform Abstract: Synthesis and Biological Activities of Some Pseudo‐Peptide Analogues of Tetragastrin: The Importance of the Peptide Backbone.

Abstract

Die Pseudopeptide (I) werden synthetisiert und auf Affinität zu Gastrin‐Rezeptoren untersucht.

Substrate and Reaction Specificity of Mycobacterium tuberculosis Cytochrome P450 CYP121

“…Compounds 2, 3, 5, 6, and 7 were synthesized previously in our laboratory (12,14). Compounds 8, 9, 10, 11, and 15 were chemically synthesized by adapting previously published procedures (17)(18)(19)(20)(21). The synthesis strategies are shown in Fig.…”

“…a, piperazine, triethylamine, and 1-(benzyloxy)-4-(chloromethyl)benzene (1:2.2:10) were stirred in tetrahydrofuran for 18 h at room temperature, evaporated to dryness, and subjected to chromatography on SiO 2 in ethyl acetate/hexane (7:3, v/v); b, dissolution in methanol/ethanol (8:2, v/v), hydrogenation with 5 mg 10% palladium on carbon, drying under vacuum, purification by RP-HPLC. C, the synthesis of 15 was adapted from previous publications describing reductive amination (18,20,21) and liquid phase peptide synthesis (19). a, incubation in dimethylformamide/AcOH for 0.5 h at room temperature, cooled to 0°C, NaBH 3 CN, 16 h at room temperature, evaporation under reduced pressure at temperature Ͻ40°C; b, dissolution in methanol, 10% palladium on carbon overnight under 3.3 bars of H 2 , evaporation to dryness; c, dissolution in HCOOH, 2 h at room temperature with stirring, evaporation under reduced pressure (temperature Ͻ40°C), addition of triethylamine and dry dimethylformamide and stirring for 16 h at room temperature, evaporation under reduced pressure, purification by RP-HPLC.…”

International Union of Pharmacology. LXVIII. Mammalian Bombesin Receptors: Nomenclature, Distribution, Pharmacology, Signaling, and Functions in Normal and Disease States

“…In 1988 Coy and coworkers reported a new class of BB 2 receptor antagonists by substituting pseudopeptide bonds ( bonds) (i.e., each CONH group one at a time replaced by CH 2 NH) into the COOH terminus of bombesin, a strategy that had been used successfully to make antagonists for gastrin, secretin, and substance P (Martinez et al, 1985;Rodriguez et al, 1986;Coy et al, 1988;Qian et al, 1989;Haffar et al, 1991) (Fig. 1; Table 2).…”

Systematic solid‐phase synthesis of linear pseudooligolysines containing multiple adjacent CH2NH amide bond surrogates: potential agents for gene delivery

“…It is noteworthy that the CH 2 NH group has already been employed successfully to obtain biologically active peptides such as antagonists of bombesin (13), secretin (14), substance P (15) and gastrin receptors (16).…”