Synthesis of human pancreatic growth hormone-releasing factor and two omission analogs by segment-coupling method in aqueous solution.
The human growth hormone-releasing factor (GRF) peptides [GlyS15]-GRF-(1-15) (IV), trifluoroacetyl-GRF-(20-44) (VI), trifluoroacetyl-GRF-(18-44) (VIII), and trifluoroacetyl-GRF-(16-44) (X) were synthesized by the solid-phase method. Each of the peptides was reacted with citraconic anhydride and the trifluoroacetyl group was removed by reaction with 10% hydrazine in water. The citraconylated GRF-(1-15) peptide was coupled to the (20-44), (18-44) or (16-44) peptides by reaction with silver nitrate/N-hydroxysuccinimide to give GRF-(1-15)-(20-44) (XII), GRF-(1-15)-(18-44) (XIII), or GRF-(1-44), respectively. GRF-(1-44) was shown to stimulate the release of rat growth hormone from rat pituitary cells with an ED50 = 8.8 X 10(-11)M. Peptides XII and XIII were inactive, either as agonists or as antagonists of the action of GRF-(1-44).
D000818:Animals; D001681:Biological Assay; D002478:Cells, Cultured; D013006:Growth Hormone / Q000378:metabolism; D013007:Growth Hormone-Releasing Hormone / Q000138:chemical synthesis*; D006801:Humans; D010179:Pancreas / Q000502:physiology; D010903:Pituitary Gland, Anterior / Q000378:metabolism; D051381:Rats; D013329:Structure-Activity Relationship
D013006:Growth Hormone; D013007:Growth Hormone-Releasing Hormone