A chemo-enzymatic expeditious route to racemic dihexanoyl (2R*,3R*,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2 S,3S,4 S )-DHMEQ

Ryohei Kobayashi; Kengo Hanaya; Mitsuru Shoji; Kazuo Umezawa; Takeshi Sugai

doi:10.1248/cpb.c12-00417

A chemo-enzymatic expeditious route to racemic dihexanoyl (2R,3R,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2 S,3S,4 S )-DHMEQ

Ryohei Kobayashi, Kengo Hanaya, Mitsuru Shoji, Kazuo Umezawa, Takeshi Sugai

School of Pharmaceutical Sciences

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

8 Citations (Scopus)

Abstract

In order to synthesize the potent nuclear factor (NF)- κB inhibitor, (2S ,3 S ,4 S )-dehydroxymethylepoxyquinomycin (DHMEQ), in a large scale, a new route for its corresponding racemic precursor, dihexanoyl (2R*,3R*, 4R*)- DHMEQ, was developed. By employing both hydroquinone and benzoquinone intermediates, the total yield, reproducibility, and synthetic steps were improved and the synthetic cost was reduced.

Original language	English
Pages (from-to)	1220-1223
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	60
Issue number	9
DOIs	https://doi.org/10.1248/cpb.c12-00417
Publication status	Published - 2012 Sept

Keywords

Benzoquinone
Dehydroxymethylepoxyquinomycin
Epoxidation
Hydroquinone
Oxidation
Process chemistry

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.c12-00417

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Kobayashi, R., Hanaya, K., Shoji, M., Umezawa, K., & Sugai, T. (2012). A chemo-enzymatic expeditious route to racemic dihexanoyl (2R*,3R*,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2 S,3S,4 S )-DHMEQ. Chemical and Pharmaceutical Bulletin, 60(9), 1220-1223. https://doi.org/10.1248/cpb.c12-00417

A chemo-enzymatic expeditious route to racemic dihexanoyl (2R*,3R*,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2 S,3S,4 S )-DHMEQ. / Kobayashi, Ryohei; Hanaya, Kengo; Shoji, Mitsuru et al.
In: Chemical and Pharmaceutical Bulletin, Vol. 60, No. 9, 09.2012, p. 1220-1223.

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

Kobayashi, R, Hanaya, K, Shoji, M, Umezawa, K & Sugai, T 2012, 'A chemo-enzymatic expeditious route to racemic dihexanoyl (2R*,3R*,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2 S,3S,4 S )-DHMEQ', Chemical and Pharmaceutical Bulletin, vol. 60, no. 9, pp. 1220-1223. https://doi.org/10.1248/cpb.c12-00417

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