Total synthesis and structure revision of the (-)-maduropeptin chromophore

Kazuo Komano; Satoshi Shimamura; Yutaro Norizuki; Donglin Zhao; Chizuko Kabuto; Itaru Sato; Masahiro Hirama

doi:10.1021/ja905397p

Total synthesis and structure revision of the (-)-maduropeptin chromophore

Kazuo Komano, Satoshi Shimamura, Yutaro Norizuki, Donglin Zhao, Chizuko Kabuto, Itaru Sato, Masahiro Hirama

SCI - Research and Analytical Center for Giant Molecules

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

19 Citations (Scopus)

Abstract

(Chemical Equation Presented) The proposed structure of the maduropeptin chromophore, the biologically active component of the highly potent chromoprotein antitumor antibiotics, was stereoselectively synthesized but did not satisfy the spectra of the natural product. We demonstrated that the correct structure is diastereomeric, which possesses an antipodal sugar moiety.

Original language	English
Pages (from-to)	12072-12073
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	34
DOIs	https://doi.org/10.1021/ja905397p
Publication status	Published - 2009 Sep 2

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja905397p

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abstract = "(Chemical Equation Presented) The proposed structure of the maduropeptin chromophore, the biologically active component of the highly potent chromoprotein antitumor antibiotics, was stereoselectively synthesized but did not satisfy the spectra of the natural product. We demonstrated that the correct structure is diastereomeric, which possesses an antipodal sugar moiety.",

author = "Kazuo Komano and Satoshi Shimamura and Yutaro Norizuki and Donglin Zhao and Chizuko Kabuto and Itaru Sato and Masahiro Hirama",

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AU - Komano, Kazuo

AU - Shimamura, Satoshi

AU - Norizuki, Yutaro

AU - Zhao, Donglin

AU - Kabuto, Chizuko

AU - Sato, Itaru

AU - Hirama, Masahiro

PY - 2009/9/2

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N2 - (Chemical Equation Presented) The proposed structure of the maduropeptin chromophore, the biologically active component of the highly potent chromoprotein antitumor antibiotics, was stereoselectively synthesized but did not satisfy the spectra of the natural product. We demonstrated that the correct structure is diastereomeric, which possesses an antipodal sugar moiety.

AB - (Chemical Equation Presented) The proposed structure of the maduropeptin chromophore, the biologically active component of the highly potent chromoprotein antitumor antibiotics, was stereoselectively synthesized but did not satisfy the spectra of the natural product. We demonstrated that the correct structure is diastereomeric, which possesses an antipodal sugar moiety.

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Total synthesis and structure revision of the (-)-maduropeptin chromophore

Abstract

ASJC Scopus subject areas

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