Antidiuretic and pressor activities of vasopressin analogs with L-alaninamide and D-alaninamide substitutions at position 9.

Analogs of arginine vasopressin (AVP) and lysine vasopressin (LVP)--with an L-alaninamide residue or a D-alaninamide residue replacing the naturally occurring glycinamide in position 9--lose virtually all pressor activity but retain from 10 to 70% of the antidiuretic activity of their parent hormones. These findings, in conjunction with the data of others on the biological consequences of alterations in positions 7 and 8, show that the antidiuretic receptor will tolerate considerably more structural alteration in the C-terminal tripeptide "tail" of the vasopressins than will the pressor receptor.