4Z- and 4E-12-deoxydihydrokromycins, two naturally occurring kromycin aglycones of pikromycin from Streptomyces sp.

Inho Yang; Jisoo Yoon; Dayoung Kim; Dongyup Hahn; Sang Jip Nam; William Fenical

doi:10.1016/j.tetlet.2017.03.088

4Z- and 4E-12-deoxydihydrokromycins, two naturally occurring kromycin aglycones of pikromycin from Streptomyces sp.

Inho Yang, Jisoo Yoon, Dayoung Kim, Dongyup Hahn, Sang Jip Nam, William Fenical

Department of Chemistry & Nanoscience

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

2 Scopus citations

Abstract

HPLC–UV guided isolation for the culture broth extract of the marine-derived bacterium Streptomyces sp. has led to the two 14-membered macrolides, 4Z- (1) and 4E-12-dehydroxykromycins (2). The chemical structures of compounds 1 and 2 were elucidated by spectral data, while the absolute stereochemistry of 1 and 2 were determined by application of circular dichroism (CD) and analysis of X-ray crystallographic data.

Original language	English
Pages (from-to)	2322-2324
Number of pages	3
Journal	Tetrahedron Letters
Volume	58
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2017.03.088
State	Published - 2017

Bibliographical note

Funding Information:
The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT & Future Planning (NRF-2014R1A1A1003492), and by the U.S. National Cancer Institute (NIH) under grant R37CA044848 and instrument grant 1 S10 OD0106400-01A1 (HR-LC?MS, both to W.F.). We thank Drs C. Moore and A. Rheingold for assistance with the crystallization and the acquisition of X-ray diffraction data.

Funding Information:
The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT & Future Planning (NRF-2014R1A1A1003492), and by the U.S. National Cancer Institute (NIH) under grant R37CA044848 and instrument grant 1 S10 OD0106400-01A1 (HR-LC–MS, both to W.F.). We thank Drs C. Moore and A. Rheingold for assistance with the crystallization and the acquisition of X-ray diffraction data.

Publisher Copyright:
© 2017

Keywords

14-Membered macrolide
Kromycin derivative
Marine-derived Streptomyces sp.
Pikromycin aglycone

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10.1016/j.tetlet.2017.03.088

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title = "4Z- and 4E-12-deoxydihydrokromycins, two naturally occurring kromycin aglycones of pikromycin from Streptomyces sp.",

abstract = "HPLC–UV guided isolation for the culture broth extract of the marine-derived bacterium Streptomyces sp. has led to the two 14-membered macrolides, 4Z- (1) and 4E-12-dehydroxykromycins (2). The chemical structures of compounds 1 and 2 were elucidated by spectral data, while the absolute stereochemistry of 1 and 2 were determined by application of circular dichroism (CD) and analysis of X-ray crystallographic data.",

keywords = "14-Membered macrolide, Kromycin derivative, Marine-derived Streptomyces sp., Pikromycin aglycone",

author = "Inho Yang and Jisoo Yoon and Dayoung Kim and Dongyup Hahn and Nam, {Sang Jip} and William Fenical",

note = "Funding Information: The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT & Future Planning (NRF-2014R1A1A1003492), and by the U.S. National Cancer Institute (NIH) under grant R37CA044848 and instrument grant 1 S10 OD0106400-01A1 (HR-LC?MS, both to W.F.). We thank Drs C. Moore and A. Rheingold for assistance with the crystallization and the acquisition of X-ray diffraction data. Funding Information: The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT & Future Planning (NRF-2014R1A1A1003492), and by the U.S. National Cancer Institute (NIH) under grant R37CA044848 and instrument grant 1 S10 OD0106400-01A1 (HR-LC–MS, both to W.F.). We thank Drs C. Moore and A. Rheingold for assistance with the crystallization and the acquisition of X-ray diffraction data. Publisher Copyright: {\textcopyright} 2017",

year = "2017",

doi = "10.1016/j.tetlet.2017.03.088",

language = "English",

volume = "58",

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journal = "Tetrahedron Letters",

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AU - Yang, Inho

AU - Yoon, Jisoo

AU - Kim, Dayoung

AU - Hahn, Dongyup

AU - Nam, Sang Jip

AU - Fenical, William

N1 - Funding Information: The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT & Future Planning (NRF-2014R1A1A1003492), and by the U.S. National Cancer Institute (NIH) under grant R37CA044848 and instrument grant 1 S10 OD0106400-01A1 (HR-LC?MS, both to W.F.). We thank Drs C. Moore and A. Rheingold for assistance with the crystallization and the acquisition of X-ray diffraction data. Funding Information: The present study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Science, ICT & Future Planning (NRF-2014R1A1A1003492), and by the U.S. National Cancer Institute (NIH) under grant R37CA044848 and instrument grant 1 S10 OD0106400-01A1 (HR-LC–MS, both to W.F.). We thank Drs C. Moore and A. Rheingold for assistance with the crystallization and the acquisition of X-ray diffraction data. Publisher Copyright: © 2017

PY - 2017

Y1 - 2017

N2 - HPLC–UV guided isolation for the culture broth extract of the marine-derived bacterium Streptomyces sp. has led to the two 14-membered macrolides, 4Z- (1) and 4E-12-dehydroxykromycins (2). The chemical structures of compounds 1 and 2 were elucidated by spectral data, while the absolute stereochemistry of 1 and 2 were determined by application of circular dichroism (CD) and analysis of X-ray crystallographic data.

AB - HPLC–UV guided isolation for the culture broth extract of the marine-derived bacterium Streptomyces sp. has led to the two 14-membered macrolides, 4Z- (1) and 4E-12-dehydroxykromycins (2). The chemical structures of compounds 1 and 2 were elucidated by spectral data, while the absolute stereochemistry of 1 and 2 were determined by application of circular dichroism (CD) and analysis of X-ray crystallographic data.

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KW - Kromycin derivative

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JO - Tetrahedron Letters

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IS - 24

ER -

4Z- and 4E-12-deoxydihydrokromycins, two naturally occurring kromycin aglycones of pikromycin from Streptomyces sp.

Abstract

Bibliographical note

Keywords

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