JBIR-155, a Specific Class D β-Lactamase Inhibitor of Microbial Origin

Takehiro Nishimura; Teppei Kawahara; Noritaka Kagaya; Yusuke Ogura; Hirosato Takikawa; Hikaru Suenaga; Masaatsu Adachi; Takatsugu Hirokawa; Takayuki Doi; Kazuo Shin-Ya

doi:10.1021/acs.orglett.1c01352

JBIR-155, a Specific Class D β-Lactamase Inhibitor of Microbial Origin

Takehiro Nishimura, Teppei Kawahara, Noritaka Kagaya, Yusuke Ogura, Hirosato Takikawa, Hikaru Suenaga, Masaatsu Adachi, Takatsugu Hirokawa, Takayuki Doi, Kazuo Shin-Ya

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

3 Citations (Scopus)

Abstract

We discovered JBIR-155 as a novel specific class D β-lactamase inhibitor from Streptomyces polymachus SoB100815Hv02. JBIR-155 consists of a 6-oxabicyclo[3.2.0]heptan-7-one skeleton and a long unsaturated alkyl chain moiety of which absolute configuration was determined by spectroscopic data, modified Mosher's method, and analyses of the relative configuration of chemically modified derivative. JBIR-155 specifically exhibited inhibitory activity against the class D β-lactamase, with an IC50 value of 0.36 μM.

Original language	English
Pages (from-to)	4415-4419
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.1c01352
Publication status	Published - 2021 Jun 4
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.1c01352

Cite this

@article{23d61e811b1642418d3e2722bb56afed,

title = "JBIR-155, a Specific Class D β-Lactamase Inhibitor of Microbial Origin",

abstract = "We discovered JBIR-155 as a novel specific class D β-lactamase inhibitor from Streptomyces polymachus SoB100815Hv02. JBIR-155 consists of a 6-oxabicyclo[3.2.0]heptan-7-one skeleton and a long unsaturated alkyl chain moiety of which absolute configuration was determined by spectroscopic data, modified Mosher's method, and analyses of the relative configuration of chemically modified derivative. JBIR-155 specifically exhibited inhibitory activity against the class D β-lactamase, with an IC50 value of 0.36 μM.",

author = "Takehiro Nishimura and Teppei Kawahara and Noritaka Kagaya and Yusuke Ogura and Hirosato Takikawa and Hikaru Suenaga and Masaatsu Adachi and Takatsugu Hirokawa and Takayuki Doi and Kazuo Shin-Ya",

note = "Funding Information: All four classes of β-lactamase enzymes were kindly provided by Meiji Seika Pharma Co., Ltd. The computational studies were supported by the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from the Japan Agency for Medical Research and Development (AMED, JP18am0101114). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = jun,

day = "4",

doi = "10.1021/acs.orglett.1c01352",

language = "English",

volume = "23",

pages = "4415--4419",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - JBIR-155, a Specific Class D β-Lactamase Inhibitor of Microbial Origin

AU - Nishimura, Takehiro

AU - Kawahara, Teppei

AU - Kagaya, Noritaka

AU - Ogura, Yusuke

AU - Takikawa, Hirosato

AU - Suenaga, Hikaru

AU - Adachi, Masaatsu

AU - Hirokawa, Takatsugu

AU - Doi, Takayuki

AU - Shin-Ya, Kazuo

N1 - Funding Information: All four classes of β-lactamase enzymes were kindly provided by Meiji Seika Pharma Co., Ltd. The computational studies were supported by the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from the Japan Agency for Medical Research and Development (AMED, JP18am0101114). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/6/4

Y1 - 2021/6/4

N2 - We discovered JBIR-155 as a novel specific class D β-lactamase inhibitor from Streptomyces polymachus SoB100815Hv02. JBIR-155 consists of a 6-oxabicyclo[3.2.0]heptan-7-one skeleton and a long unsaturated alkyl chain moiety of which absolute configuration was determined by spectroscopic data, modified Mosher's method, and analyses of the relative configuration of chemically modified derivative. JBIR-155 specifically exhibited inhibitory activity against the class D β-lactamase, with an IC50 value of 0.36 μM.

AB - We discovered JBIR-155 as a novel specific class D β-lactamase inhibitor from Streptomyces polymachus SoB100815Hv02. JBIR-155 consists of a 6-oxabicyclo[3.2.0]heptan-7-one skeleton and a long unsaturated alkyl chain moiety of which absolute configuration was determined by spectroscopic data, modified Mosher's method, and analyses of the relative configuration of chemically modified derivative. JBIR-155 specifically exhibited inhibitory activity against the class D β-lactamase, with an IC50 value of 0.36 μM.

UR - http://www.scopus.com/inward/record.url?scp=85107712444&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85107712444&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c01352

DO - 10.1021/acs.orglett.1c01352

M3 - Article

C2 - 34029112

AN - SCOPUS:85107712444

SN - 1523-7060

VL - 23

SP - 4415

EP - 4419

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

JBIR-155, a Specific Class D β-Lactamase Inhibitor of Microbial Origin

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this