title: Synthesis and diuretic activities of pseudoproline-containing analogues of the insect kinin core pentapeptide.
abstract: C-2 dimethylated/unmethylated thiazolidine-4-carboxylic acid and C-2 dimethylated oxazolidine-4-carboxylic acid were introduced into the insect kinin core pentapeptide in place of Pro(3) , yielding three new analogues. NMR analysis revealed that the peptide bond of Phe(2) -pseudoproline (ΨPro)(3) is practically 100% in cis conformation in the case of dimethylated pseudoproline-containing analogues, about 50% cis for the thiazolidine-4-carboxylic acid analogue and about 33% cis for the parent Pro(3) peptide. The diuretic activities are consistent with the population of cis conformation of the Phe(2) -ΨPro(3) /Pro(3) peptide bonds, and the results confirm a cis Phe-Pro bond as bioactive conformation.
authors.affiliation: Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, China.
authors.forename: Bo
authors.initials: B
authors.lastname: Zhang
authors.forename: Junbin
authors.initials: J
authors.lastname: Gong
authors.forename: Yinliang
authors.initials: Y
authors.lastname: Yang
authors.forename: Shouliang
authors.initials: S
authors.lastname: Dong
mesh_terms: D000818:Animals; D002264:Carboxylic Acids / Q000737:chemistry; D004232:Diuretics / Q000737:chemistry / Q000494:pharmacology*; D041981:Gastrointestinal Tract / Q000187:drug effects; D007313:Insecta / Q000033:anatomy & histology / Q000737:chemistry*; D007705:Kinins / Q000737:chemistry* / Q000235:genetics / Q000494:pharmacology*; D010455:Peptides / Q000737:chemistry* / Q000235:genetics / Q000494:pharmacology*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D011487:Protein Conformation; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D004232:Diuretics; D007705:Kinins; D010455:Peptides; D013844:Thiazoles; C505976:pseudoproline; D011392:Proline