Argifin; efficient solid phase total synthesis and evaluation of analogues of acyclic peptide

Toshiaki Sunazuka; Akihiro Sugawara; Kanami Iguchi; Tomoyasu Hirose; Kenichiro Nagai; Yoshihiko Noguchi; Yoshifumi Saito; Tsuyoshi Yamamoto; Hideaki Ui; Hiroaki Gouda; Kazuro Shiomi; Takeshi Watanabe; Satoshi Omura

doi:10.1016/j.bmc.2009.02.047

Argifin; efficient solid phase total synthesis and evaluation of analogues of acyclic peptide

Bioorg Med Chem. 2009 Apr 1;17(7):2751-8. doi: 10.1016/j.bmc.2009.02.047. Epub 2009 Feb 27.

Authors

Toshiaki Sunazuka¹, Akihiro Sugawara, Kanami Iguchi, Tomoyasu Hirose, Kenichiro Nagai, Yoshihiko Noguchi, Yoshifumi Saito, Tsuyoshi Yamamoto, Hideaki Ui, Hiroaki Gouda, Kazuro Shiomi, Takeshi Watanabe, Satoshi Omura

Affiliation

¹ Kitasato Institute for Life Sciences, Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan. sunazuka@lisci.kitasato-u.ac.jp

PMID: 19297173
DOI: 10.1016/j.bmc.2009.02.047

Abstract

An effective solid phase synthesis of Argifin, providing subsequent access to effective synthesis of analogues, was developed in 13% overall yield, as well as elucidating structure-activity relationships. The novel acyclic peptide 18b, prepared from a synthetic intermediate of Argifin, was found to be 70 times more potent as an inhibitor of Serratia marcescens chitinases B than Argifin itself.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
Chitinases / antagonists & inhibitors*
Chitinases / metabolism
Peptides / chemical synthesis*
Peptides / chemistry
Peptides / pharmacology
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry
Peptides, Cyclic / pharmacology
Serratia marcescens / enzymology
Structure-Activity Relationship

Substances

Peptides
Peptides, Cyclic
argifin
Chitinases