Absolute configuration of iminimycin B, a new indolizidine alkaloid, from Streptomyces griseus OS-3601

Takuji Nakashima; Rei Miyano; Hirotaka Matsuo; Masato Iwatsuki; Tatsuya Shirahata; Yoshinori Kobayashi; Kazuro Shiomi; George A. Petersson; Yōko Takahashi; Satoshi Ōmura

doi:10.1016/j.tetlet.2016.06.040

Absolute configuration of iminimycin B, a new indolizidine alkaloid, from Streptomyces griseus OS-3601

Takuji Nakashima^*, Rei Miyano, Hirotaka Matsuo, Masato Iwatsuki, Tatsuya Shirahata, Yoshinori Kobayashi, Kazuro Shiomi, George A. Petersson, Yōko Takahashi, Satoshi Ōmura

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

Iminimycin B, a novel indolizine alkaloid featuring a rare pyridinium, was isolated from the cultured broth of a streptomycin-producing strain, Streptomyces griseus OS-3601, through a physicochemical screening method. Its structure was elucidated on the basis of mass and NMR analyses. Stereochemical assignment of iminimycin B was archived by NMR studies, electronic circular dichroism (ECD) analysis, and advanced Marfey's method.

Original language	English
Pages (from-to)	3284-3286
Number of pages	3
Journal	Tetrahedron Letters
Volume	57
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2016.06.040
Publication status	Published - 2016
Externally published	Yes

Keywords

Iminimycin
Indolizidine
Pyridinium
Streptomyces

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2016.06.040

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title = "Absolute configuration of iminimycin B, a new indolizidine alkaloid, from Streptomyces griseus OS-3601",

abstract = "Iminimycin B, a novel indolizine alkaloid featuring a rare pyridinium, was isolated from the cultured broth of a streptomycin-producing strain, Streptomyces griseus OS-3601, through a physicochemical screening method. Its structure was elucidated on the basis of mass and NMR analyses. Stereochemical assignment of iminimycin B was archived by NMR studies, electronic circular dichroism (ECD) analysis, and advanced Marfey's method.",

keywords = "Iminimycin, Indolizidine, Pyridinium, Streptomyces",

author = "Takuji Nakashima and Rei Miyano and Hirotaka Matsuo and Masato Iwatsuki and Tatsuya Shirahata and Yoshinori Kobayashi and Kazuro Shiomi and Petersson, {George A.} and Yōko Takahashi and Satoshi Ōmura",

note = "Funding Information: We are grateful to Drs Kenichiro Nagai and Noriko Sato, School of Pharmacy, Kitasato University, for measurement of MS and NMR spectra. This study was supported by funds from the Institute for Fermentation , Osaka (IFO), Japan. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tetlet.2016.06.040",

language = "English",

volume = "57",

pages = "3284--3286",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "30",

}

TY - JOUR

T1 - Absolute configuration of iminimycin B, a new indolizidine alkaloid, from Streptomyces griseus OS-3601

AU - Nakashima, Takuji

AU - Miyano, Rei

AU - Matsuo, Hirotaka

AU - Iwatsuki, Masato

AU - Shirahata, Tatsuya

AU - Kobayashi, Yoshinori

AU - Shiomi, Kazuro

AU - Petersson, George A.

AU - Takahashi, Yōko

AU - Ōmura, Satoshi

N1 - Funding Information: We are grateful to Drs Kenichiro Nagai and Noriko Sato, School of Pharmacy, Kitasato University, for measurement of MS and NMR spectra. This study was supported by funds from the Institute for Fermentation , Osaka (IFO), Japan. Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - Iminimycin B, a novel indolizine alkaloid featuring a rare pyridinium, was isolated from the cultured broth of a streptomycin-producing strain, Streptomyces griseus OS-3601, through a physicochemical screening method. Its structure was elucidated on the basis of mass and NMR analyses. Stereochemical assignment of iminimycin B was archived by NMR studies, electronic circular dichroism (ECD) analysis, and advanced Marfey's method.

AB - Iminimycin B, a novel indolizine alkaloid featuring a rare pyridinium, was isolated from the cultured broth of a streptomycin-producing strain, Streptomyces griseus OS-3601, through a physicochemical screening method. Its structure was elucidated on the basis of mass and NMR analyses. Stereochemical assignment of iminimycin B was archived by NMR studies, electronic circular dichroism (ECD) analysis, and advanced Marfey's method.

KW - Iminimycin

KW - Indolizidine

KW - Pyridinium

KW - Streptomyces

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UR - http://www.scopus.com/inward/citedby.url?scp=84976871458&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2016.06.040

DO - 10.1016/j.tetlet.2016.06.040

M3 - Article

AN - SCOPUS:84976871458

SN - 0040-4039

VL - 57

SP - 3284

EP - 3286

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

Absolute configuration of iminimycin B, a new indolizidine alkaloid, from Streptomyces griseus OS-3601

Abstract

Keywords

ASJC Scopus subject areas

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