Zamamistatin, a significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea

Noboru Takada; Reiko Watanabe; Kiyotake Suenaga; Kaoru Yamada; Katsuhiro Ueda; Masaki Kita; Daisuke Uemura

doi:10.1016/S0040-4039(01)00993-5

Zamamistatin, a significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea

Noboru Takada
, Reiko Watanabe
, Kiyotake Suenaga
, Kaoru Yamada
, Katsuhiro Ueda
, Masaki Kita
, Daisuke Uemura

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

50 Citations (Scopus)

Abstract

Zamamistatin was isolated from the Okinawan sponge Pseudoceratina purpurea. It was determined to be a novel bromotyrosine derivative by careful analysis of 2D NMR spectra and comparison of its ¹H NMR spectrum with those of structurally related compounds. The absolute stereostructure of zamamistatin was determined by the modified Mosher's method. Zamamistatin exhibited significant antibacterial activity against Rhodospirillum salexigens, which has adhering properties.

Original language	English
Pages (from-to)	5265-5267
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(01)00993-5
Publication status	Published - 2001 Jul 30
Externally published	Yes

Keywords

Absolute stereochemistry
Antibacterial activity
Antifouling agent
Isolation
Structural determination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)00993-5

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title = "Zamamistatin, a significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea",

abstract = "Zamamistatin was isolated from the Okinawan sponge Pseudoceratina purpurea. It was determined to be a novel bromotyrosine derivative by careful analysis of 2D NMR spectra and comparison of its 1H NMR spectrum with those of structurally related compounds. The absolute stereostructure of zamamistatin was determined by the modified Mosher's method. Zamamistatin exhibited significant antibacterial activity against Rhodospirillum salexigens, which has adhering properties.",

keywords = "Absolute stereochemistry, Antibacterial activity, Antifouling agent, Isolation, Structural determination",

author = "Noboru Takada and Reiko Watanabe and Kiyotake Suenaga and Kaoru Yamada and Katsuhiro Ueda and Masaki Kita and Daisuke Uemura",

note = "Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (No. 11558079) and Scientific Research on Priority Areas (A) (No. 12045235) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. The authors are indebted to Wako Pure Chemical Industries Ltd. and Banyu Pharmaceutical Co. Ltd. for their financial support. They like to thank Professor P. R. Bergquist of the University of Auckland for identifying the sponge. They would also like to thank Professors R. Noyori and M. Kitamura (COE, Nagoya University) for allowing them to use the NMR instruments.",

year = "2001",

month = jul,

day = "30",

doi = "10.1016/S0040-4039(01)00993-5",

language = "English",

volume = "42",

pages = "5265--5267",

journal = "Tetrahedron Letters",

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number = "31",

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TY - JOUR

T1 - Zamamistatin, a significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea

AU - Takada, Noboru

AU - Watanabe, Reiko

AU - Suenaga, Kiyotake

AU - Yamada, Kaoru

AU - Ueda, Katsuhiro

AU - Kita, Masaki

AU - Uemura, Daisuke

N1 - Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (No. 11558079) and Scientific Research on Priority Areas (A) (No. 12045235) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. The authors are indebted to Wako Pure Chemical Industries Ltd. and Banyu Pharmaceutical Co. Ltd. for their financial support. They like to thank Professor P. R. Bergquist of the University of Auckland for identifying the sponge. They would also like to thank Professors R. Noyori and M. Kitamura (COE, Nagoya University) for allowing them to use the NMR instruments.

PY - 2001/7/30

Y1 - 2001/7/30

N2 - Zamamistatin was isolated from the Okinawan sponge Pseudoceratina purpurea. It was determined to be a novel bromotyrosine derivative by careful analysis of 2D NMR spectra and comparison of its 1H NMR spectrum with those of structurally related compounds. The absolute stereostructure of zamamistatin was determined by the modified Mosher's method. Zamamistatin exhibited significant antibacterial activity against Rhodospirillum salexigens, which has adhering properties.

AB - Zamamistatin was isolated from the Okinawan sponge Pseudoceratina purpurea. It was determined to be a novel bromotyrosine derivative by careful analysis of 2D NMR spectra and comparison of its 1H NMR spectrum with those of structurally related compounds. The absolute stereostructure of zamamistatin was determined by the modified Mosher's method. Zamamistatin exhibited significant antibacterial activity against Rhodospirillum salexigens, which has adhering properties.

KW - Absolute stereochemistry

KW - Antibacterial activity

KW - Antifouling agent

KW - Isolation

KW - Structural determination

UR - https://www.scopus.com/pages/publications/0035974411

UR - https://www.scopus.com/pages/publications/0035974411#tab=citedBy

U2 - 10.1016/S0040-4039(01)00993-5

DO - 10.1016/S0040-4039(01)00993-5

M3 - Article

AN - SCOPUS:0035974411

SN - 0040-4039

VL - 42

SP - 5265

EP - 5267

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Zamamistatin, a significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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