title: Novel protocol for the chemical synthesis of crustacean hyperglycemic hormone analogues--an efficient experimental tool for studying their functions.
abstract: The crustacean Hyperglycemic Hormone (cHH) is present in many decapods in different isoforms, whose specific biological functions are still poorly understood. Here we report on the first chemical synthesis of three distinct isoforms of the cHH of Astacus leptodactylus carried out by solid phase peptide synthesis coupled to native chemical ligation. The synthetic 72 amino acid long peptide amides, containing L- or D-Phe³ and (Glp¹, D-Phe³) were tested for their biological activity by means of homologous in vivo bioassays. The hyperglycemic activity of the D-isoforms was significantly higher than that of the L-isoform, while the presence of the N-terminal Glp residue had no influence on the peptide activity. The results show that the presence of D-Phe³ modifies the cHH functionality, contributing to the diversification of the hormone pool.
authors.affiliation: Department of Life Sciences, University of Trieste, Trieste, Italy. alessandro.mosco@phd.units.it
authors.forename: Alessandro
authors.initials: A
authors.lastname: Mosco
authors.forename: Vientsislav
authors.initials: V
authors.lastname: Zlatev
authors.forename: Corrado
authors.initials: C
authors.lastname: Guarnaccia
authors.forename: Sándor
authors.initials: S
authors.lastname: Pongor
authors.forename: Antonella
authors.initials: A
authors.lastname: Campanella
authors.forename: Sotir
authors.initials: S
authors.lastname: Zahariev
authors.forename: Piero G
authors.initials: PG
authors.lastname: Giulianini
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D060829:Arthropod Proteins / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003400:Astacoidea / Q000737:chemistry / Q000187:drug effects; D001681:Biological Assay; D002851:Chromatography, High Pressure Liquid; D056148:Chromatography, Reverse-Phase; D005947:Glucose / Q000378:metabolism; D006943:Hyperglycemia / Q000473:pathology; D007447:Invertebrate Hormones / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007536:Isomerism; D008969:Molecular Sequence Data; D009419:Nerve Tissue Proteins / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010455:Peptides / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D060829:Arthropod Proteins; D007447:Invertebrate Hormones; D009419:Nerve Tissue Proteins; D010455:Peptides; C015947:hyperglycemic hormone, crustacean; D005947:Glucose