Correct disulfide pairing is required for the biological activity of crustacean androgenic gland hormone (AGH): synthetic studies of AGH.
Androgenic gland hormone (AGH) of the woodlouse, Armadillidium vulgare, is a heterodimeric glycopeptide. In this study, we synthesized AGH with a homogeneous N-linked glycan using the expressed protein ligation method. Unexpectedly, disulfide bridge arrangement of a semisynthetic peptide differed from that of a recombinant peptide prepared in a baculovirus expression system, and the semisynthetic peptide showed no biological activity in vivo. To confirm that the loss of biological activity resulted from disulfide bond isomerization, AGH with a GlcNAc moiety was chemically synthesized by the selective disulfide formation. This synthetic AGH showed biological activity in vivo. These results indicate that the native conformation of AGH is not the most thermodynamically stable form, and correct disulfide linkages are important for conferring AGH activity.
Katayama
Hidekazu
H
Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 1117 Kitakaname, Hiratsuka, Kanagawa 259-1292, Japan. katay@hotmail.co.jp
Hojo
Hironobu
H
Ohira
Tsuyoshi
T
Ishii
Akira
A
Nozaki
Takamichi
T
Goto
Kiyomi
K
Nakahara
Yuko
Y
Takahashi
Tetsuo
T
Hasegawa
Yuriko
Y
Nagasawa
Hiromichi
H
Nakahara
Yoshiaki
Y
D000818:Animals; D003445:Crustacea; D004591:Electrophoresis, Polyacrylamide Gel; D042341:Gonadal Hormones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D015394:Molecular Structure; D013816:Thermodynamics
D042341:Gonadal Hormones; C053644:androgenic gland hormone (Armadillidium)