The hydrophobicity in a chemically modified side-chain of cysteine residues of thanatin is related to antimicrobial activity against Micrococcus luteus.
The chemically modified thanatins with the methyl group (CH(3)), ethyl group (C(2)H(5)), and normal-octyl group (C(8)H(17)) at the side-chain of cysteine residues were synthesized. The octyl group modified form exhibited 8-fold higher antimicrobial activity against Micrococcus luteus than wild type thanatin. It was found that there was an equilateral correlation between antimicrobial activity and side-chain hydrophobicity at the cysteine residues in thanatin.
Orikasa
Yoshitake
Y
Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido, Japan.
Ichinohe
Kenta
K
Saito
Junki
J
Hashimoto
Shigeki
S
Matsumoto
Ken'ichiro
K
Ooi
Toshihiko
T
Taguchi
Seiichi
S
D000595:Amino Acid Sequence; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D023181:Antimicrobial Cationic Peptides; D003545:Cysteine / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects*; D008969:Molecular Sequence Data; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D023181:Antimicrobial Cationic Peptides; D010456:Peptides, Cyclic; C098076:thanatin; D003545:Cysteine