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1 2001

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New Proctolin Analogues Modified by the Novel D- or L-Phenylglycine Derivatives. Synthesis and Biological Studies

Szeszel-Fedorowicz W., Lisowski M., Rosiński G., Issberner J., Osborne R., Konopińska D.

Polish Journal of Chemistry

2001

Vol. 75, nr 3

411-417

New analogues of insect neuromodulator proctolin (H-Arg-Tyr-Leu-Pro-Thr-OH), modified in position 2 of the peptide chain by L- or D-phenylglycine and its 4-substituted derivatives were synthesized. For modification of proctolin a series of novel L- or D-phenylglycine derivatives H-Phg(4-NO2)-OH (1), Boc-Phg(4-NO2)-OH (2), Boc- Phg(4-Me2N)-OH (3), H-Phg(4-OBzl)-OH (4), Boc-Phg(4-OBzl)-OH (5), H-D-Phg(4-NO2)-OH (6), Boc-D-Phg(4-NO2,)-OH (7), Boc-D-Phg(4-Me2N)-OH (8), were used. The following proctolin analogues were synthesized: H-Arg-Phg-Leu-Pro- Thr-OH (9), H-Arg-D-Phg-Leu-Pro-Thr-OH (10), H-Arg-Phg(4-OH)-Leu-Pro-Thr-OH (11), H-Arg-D-Phg(4-OH)-Leu-Pro-Thr-OH (12), H-Arg-Phg(4-NO2)-Leu- Pro-Thr-OH (13), H-Arg-D-Phg(4-NO2)-Leu-Pro-Thr-OH (14), H-Arg- Phg(4-NH2)-Leu-Pro-Thr-OH (15), H-Arg-D-Phg(4-NH2)-Leu-Pro-Thr-OH (16), H-Arg-Phg(4-NMe2)-Leu-Pro-Thr-OH (17), H-Arg-D-Phg(4-NMe2)-Leu-Pro-Thr-OH (18). Myotropic activity of proctolin analogues 9-18 was assayed in vitro on the semi-isolated heart of the mealworm Tenebrio molitor and on the foregut of the locust Schistocerca gregaria. All analogues showed a weak or none activity.