Solid-phase total synthesis of the chitinase inhibitor Argadin using a supported acetal resin.
A versatile solid-phase total synthesis was applied to the rapid preparation of Argadin, a natural product isolated and characterized as a cyclopentapeptide by our group, which possesses superior inhibitory activity against family-18 chitinases. The synthetic strategy includes peptide synthesis by using an Fmoc (9-fluorenylmethoxycarbonyl) protective group, macrolactamization, acetylguanylation and formation of hemiaminal accompanied by total deprotection, including cleavage from resin.
Hirose
Tomoyasu
T
The Kitasato Institute, Kitasato Institute for Life Science and Graduate School of Infection Control Sciences, Kitasato University, Minato-ku, Tokyo, Japan.
Sunazuka
Toshiaki
T
Sugawara
Akihiro
A
Noguchi
Yoshihiko
Y
Tanaka
Toshiaki
T
Iguchi
Kanami
K
Yamamoto
Tsuyoshi
T
Gouda
Hiroaki
H
Shiomi
Kazuro
K
Omura
Satoshi
S
D002688:Chitinases / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D011108:Polymers / Q000737:chemistry
D004791:Enzyme Inhibitors; D010456:Peptides, Cyclic; D011108:Polymers; C018801:acetal copolymer; C419444:argadin; D002688:Chitinases