A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone and its PPAR activities

Jaeyoung Ko; Hoosang Hwang; Jungwook Chin; Dongyup Hahn; Jaehwan Lee; Inho Yang; Kyoungjin Shin; Jungyeob Ham; Heonjoong Kang

doi:10.1016/j.bmcl.2010.08.069

A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone and its PPAR activities

Jaeyoung Ko
, Hoosang Hwang
, Jungwook Chin
, Dongyup Hahn
, Jaehwan Lee
, Inho Yang
, Kyoungjin Shin
, Jungyeob Ham
, Heonjoong Kang

School of Food Science & Biotechnology

Seoul National University
Korea Institute of Science and Technology

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

10 Scopus citations

Abstract

A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the α,γ dialkyl γ-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC₅₀ values of 12 μM for mPPARα, 9 μM for mPPARδ and >100 μM for mPPARγ.

Original language	English
Pages (from-to)	6017-6019
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	20
DOIs	https://doi.org/10.1016/j.bmcl.2010.08.069
State	Published - Oct 2010

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

Marine agonist
Nuclear receptor
PPAR α/δ dual agonist

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10.1016/j.bmcl.2010.08.069

Cite this

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abstract = "A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the α,γ dialkyl γ-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC50 values of 12 μM for mPPARα, 9 μM for mPPARδ and >100 μM for mPPARγ.",

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T1 - A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone and its PPAR activities

AU - Ko, Jaeyoung

AU - Hwang, Hoosang

AU - Chin, Jungwook

AU - Hahn, Dongyup

AU - Lee, Jaehwan

AU - Yang, Inho

AU - Shin, Kyoungjin

AU - Ham, Jungyeob

AU - Kang, Heonjoong

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Y1 - 2010/10

N2 - A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the α,γ dialkyl γ-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC50 values of 12 μM for mPPARα, 9 μM for mPPARδ and >100 μM for mPPARγ.

AB - A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the α,γ dialkyl γ-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC50 values of 12 μM for mPPARα, 9 μM for mPPARδ and >100 μM for mPPARγ.

KW - Marine agonist

KW - Nuclear receptor

KW - PPAR α/δ dual agonist

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M3 - Article

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AN - SCOPUS:77956933869

SN - 0960-894X

VL - 20

SP - 6017

EP - 6019

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 20

ER -

A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16- phenylhexadecanoic acid 1,4-lactone and its PPAR activities

Abstract

UN SDGs

Keywords

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