A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A

Yusuke Iijima; Asami Munakata; Kazuo Shin-ya; A. Ganesan; Takayuki Doi; Takashi Takahashi

doi:10.1016/j.tetlet.2009.04.005

A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A

Yusuke Iijima, Asami Munakata, Kazuo Shin-ya, A. Ganesan, Takayuki Doi, Takashi Takahashi

PHA - Molecular Pharmaceutical Science

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

25 Citations (Scopus)

Abstract

Spiruchostatin A, a potent histone deacetylase inhibitor, was efficiently synthesized from (3S,4R)-4-amino-3-hydroxy-5-methylhexanoic acid utilizing solid-phase peptide elongation with d-cysteine, d-alanine, and (E)-3-hydroxy-7-thio-4-heptenoic acid and solution-phase macrolactonization, followed by intramolecular disulfide formation.

Original language	English
Pages (from-to)	2970-2972
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2009.04.005
Publication status	Published - 2009 Jun 17

Keywords

Cyclic depsipeptide
Histone deacetylase
Natural product synthesis
Solid-phase synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.04.005

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title = "A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A",

abstract = "Spiruchostatin A, a potent histone deacetylase inhibitor, was efficiently synthesized from (3S,4R)-4-amino-3-hydroxy-5-methylhexanoic acid utilizing solid-phase peptide elongation with d-cysteine, d-alanine, and (E)-3-hydroxy-7-thio-4-heptenoic acid and solution-phase macrolactonization, followed by intramolecular disulfide formation.",

keywords = "Cyclic depsipeptide, Histone deacetylase, Natural product synthesis, Solid-phase synthesis",

author = "Yusuke Iijima and Asami Munakata and Kazuo Shin-ya and A. Ganesan and Takayuki Doi and Takashi Takahashi",

note = "Funding Information: This work was supported by New Energy and Industrial Technology Development Organization. ",

year = "2009",

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doi = "10.1016/j.tetlet.2009.04.005",

language = "English",

volume = "50",

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TY - JOUR

T1 - A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A

AU - Iijima, Yusuke

AU - Munakata, Asami

AU - Shin-ya, Kazuo

AU - Ganesan, A.

AU - Doi, Takayuki

AU - Takahashi, Takashi

N1 - Funding Information: This work was supported by New Energy and Industrial Technology Development Organization.

PY - 2009/6/17

Y1 - 2009/6/17

N2 - Spiruchostatin A, a potent histone deacetylase inhibitor, was efficiently synthesized from (3S,4R)-4-amino-3-hydroxy-5-methylhexanoic acid utilizing solid-phase peptide elongation with d-cysteine, d-alanine, and (E)-3-hydroxy-7-thio-4-heptenoic acid and solution-phase macrolactonization, followed by intramolecular disulfide formation.

AB - Spiruchostatin A, a potent histone deacetylase inhibitor, was efficiently synthesized from (3S,4R)-4-amino-3-hydroxy-5-methylhexanoic acid utilizing solid-phase peptide elongation with d-cysteine, d-alanine, and (E)-3-hydroxy-7-thio-4-heptenoic acid and solution-phase macrolactonization, followed by intramolecular disulfide formation.

KW - Cyclic depsipeptide

KW - Histone deacetylase

KW - Natural product synthesis

KW - Solid-phase synthesis

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U2 - 10.1016/j.tetlet.2009.04.005

DO - 10.1016/j.tetlet.2009.04.005

M3 - Article

AN - SCOPUS:65249112206

SN - 0040-4039

VL - 50

SP - 2970

EP - 2972

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A

Abstract

Keywords

ASJC Scopus subject areas

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