Solid-phase syntheses of olefin-containing inhibitors for HTLV-1 protease using the Horner-Emmons reaction.
[reaction: see text] The solid-phase Horner-Emmons reaction was successfully applied for the convenient syntheses of olefin-containing protease inhibitors. The isomerization during the solid-phase Horner-Emmons reaction can be minimized simply by the use of an appropriate amount of the base. The synthesized olefin peptides, which have an olefin gamma-amino acid at the scissile site, were found to act as effective inhibitors for the HTLV-1 protease for the first time.
Bang
Jeong Kyu
JK
Institute for Protein Research, Osaka University, 3-2 Yamadaoka, Suita, Osaka 565-0871, Japan.
Naka
Hiromi
H
Teruya
Kenta
K
Aimoto
Saburo
S
Konno
Hiroyuki
H
Nosaka
Kazuto
K
Tatsumi
Tadashi
T
Akaji
Kenichi
K
D000475:Alkenes / Q000737:chemistry*; D000595:Amino Acid Sequence; D020650:Combinatorial Chemistry Techniques; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis*; D020128:Inhibitory Concentration 50; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000494:pharmacology
D000475:Alkenes; D017320:HIV Protease Inhibitors; D009842:Oligopeptides