Argifin; efficient solid phase total synthesis and evalution 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 evalution 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

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2751-2758
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	7
DOIs	https://doi.org/10.1016/j.bmc.2009.02.047
Publication status	Published - 2009 Apr 1
Externally published	Yes

Keywords

Argifin
Chitinase
Serratia marcescens
Solid phase

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2009.02.047

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title = "Argifin; efficient solid phase total synthesis and evalution of analogues of acyclic peptide",

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.",

keywords = "Argifin, Chitinase, Serratia marcescens, Solid phase",

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

note = "Funding Information: This work was supported by the Grant of the 21st Century COE Program, Ministry of Education Culture, Sports, Science and Technology. We thank the JSPS Research Fellowships for Young Scientists to A.S. We also thank Ms. A. Nakagawa and Ms. N. Sato for various instrumental analysis. K. Nagai acknowledges a Kitasato University research grant for young researchers.",

year = "2009",

month = apr,

day = "1",

doi = "10.1016/j.bmc.2009.02.047",

language = "English",

volume = "17",

pages = "2751--2758",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "7",

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TY - JOUR

T1 - Argifin; efficient solid phase total synthesis and evalution of analogues of acyclic peptide

AU - Sunazuka, Toshiaki

AU - Sugawara, Akihiro

AU - Iguchi, Kanami

AU - Hirose, Tomoyasu

AU - Nagai, Kenichiro

AU - Noguchi, Yoshihiko

AU - Saito, Yoshifumi

AU - Yamamoto, Tsuyoshi

AU - Ui, Hideaki

AU - Gouda, Hiroaki

AU - Shiomi, Kazuro

AU - Watanabe, Takeshi

AU - Omura, Satoshi

N1 - Funding Information: This work was supported by the Grant of the 21st Century COE Program, Ministry of Education Culture, Sports, Science and Technology. We thank the JSPS Research Fellowships for Young Scientists to A.S. We also thank Ms. A. Nakagawa and Ms. N. Sato for various instrumental analysis. K. Nagai acknowledges a Kitasato University research grant for young researchers.

PY - 2009/4/1

Y1 - 2009/4/1

N2 - 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.

AB - 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.

KW - Argifin

KW - Chitinase

KW - Serratia marcescens

KW - Solid phase

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UR - http://www.scopus.com/inward/citedby.url?scp=62949225622&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2009.02.047

DO - 10.1016/j.bmc.2009.02.047

M3 - Article

C2 - 19297173

AN - SCOPUS:62949225622

SN - 0968-0896

VL - 17

SP - 2751

EP - 2758

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 7

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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