Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid

Shuhei Higashibayashi; Mitsunori Kohno; Taiji Goto; Kengo Suzuki; Tomonori Mori; Kimiko Hashimoto; Masaya Nakata

doi:10.1016/j.tetlet.2004.03.099

Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid

Shuhei Higashibayashi, Mitsunori Kohno, Taiji Goto, Kengo Suzuki, Tomonori Mori, Kimiko Hashimoto, Masaya Nakata

School of Pharmaceutical Sciences

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

34 Citations (Scopus)

Abstract

The dihydroxyisoleucine-, thiazoline- and dehydroamino acid-containing pentapeptide of the thiostrepton family of peptide antibiotics was synthesized, which featured the β-lactone opening by phenylselenylation, the vinylzinc addition to the chiral sulfinimine, the Wipf oxazoline-thiazoline conversion method and the oxidative syn-elimination of the phenylseleno group.

Original language	English
Pages (from-to)	3707-3712
Number of pages	6
Journal	Tetrahedron Letters
Volume	45
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2004.03.099
Publication status	Published - 2004 May 3

Keywords

Dihydroxyisoleucine
Sulfinimines
Thiazolines
Thioamides
Thiostrepton

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.03.099

Cite this

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title = "Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid",

abstract = "The dihydroxyisoleucine-, thiazoline- and dehydroamino acid-containing pentapeptide of the thiostrepton family of peptide antibiotics was synthesized, which featured the β-lactone opening by phenylselenylation, the vinylzinc addition to the chiral sulfinimine, the Wipf oxazoline-thiazoline conversion method and the oxidative syn-elimination of the phenylseleno group.",

keywords = "Dihydroxyisoleucine, Sulfinimines, Thiazolines, Thioamides, Thiostrepton",

author = "Shuhei Higashibayashi and Mitsunori Kohno and Taiji Goto and Kengo Suzuki and Tomonori Mori and Kimiko Hashimoto and Masaya Nakata",

note = "Funding Information: This research was supported by a Grant-in Aid for Scientific Research on Priority Areas (A) `Exploitation of Multi-Element Cyclic Molecules' from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2004",

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doi = "10.1016/j.tetlet.2004.03.099",

language = "English",

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journal = "Tetrahedron Letters",

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T2 - Synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid

AU - Higashibayashi, Shuhei

AU - Kohno, Mitsunori

AU - Goto, Taiji

AU - Suzuki, Kengo

AU - Mori, Tomonori

AU - Hashimoto, Kimiko

AU - Nakata, Masaya

N1 - Funding Information: This research was supported by a Grant-in Aid for Scientific Research on Priority Areas (A) `Exploitation of Multi-Element Cyclic Molecules' from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2004/5/3

Y1 - 2004/5/3

N2 - The dihydroxyisoleucine-, thiazoline- and dehydroamino acid-containing pentapeptide of the thiostrepton family of peptide antibiotics was synthesized, which featured the β-lactone opening by phenylselenylation, the vinylzinc addition to the chiral sulfinimine, the Wipf oxazoline-thiazoline conversion method and the oxidative syn-elimination of the phenylseleno group.

AB - The dihydroxyisoleucine-, thiazoline- and dehydroamino acid-containing pentapeptide of the thiostrepton family of peptide antibiotics was synthesized, which featured the β-lactone opening by phenylselenylation, the vinylzinc addition to the chiral sulfinimine, the Wipf oxazoline-thiazoline conversion method and the oxidative syn-elimination of the phenylseleno group.

KW - Dihydroxyisoleucine

KW - Sulfinimines

KW - Thiazolines

KW - Thioamides

KW - Thiostrepton

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JO - Tetrahedron Letters

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Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid

Abstract

Keywords

ASJC Scopus subject areas

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