Enantio- and diastereoselective total synthesis of (+)-panepophenanthrin, a ubiquitin-activating enzyme inhibitor, and biological properties of its new derivatives

Masayoshi Matsuzawa, Hideaki Kakeya, Junichiro Yamaguchi, Mitsuru Shoji, Rie Onose, Hiroyuki Osada, Yujiro Hayashi

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

The asymmetric total synthesis of (+)-panepophenanthrin, an inhibitor of ubiquitin-activating enzyme (E1), has been accomplished using catalytic asymmetric α aminoxylation of 1,4-cyclohexanedione monoethylene ketal as a key step, followed by several diastereoselective reactions. The biomimetic Diels-Alder reaction of a monomer precursor was found to proceed efficiently in water. The investigation of the biological properties of new derivatives of (+)-panepophenanthrin enabled us to develop new cell-permeable E1 inhibitors, RKTS-80, -81, and -82.

Original languageEnglish
Pages (from-to)845-851
Number of pages7
JournalChemistry - An Asian Journal
Volume1
Issue number6
DOIs
Publication statusPublished - 2006
Externally publishedYes

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Ubiquitin-Activating Enzymes
Enzyme Inhibitors
Derivatives
Biomimetics
Cycloaddition Reaction
Monomers
Water
panepophenanthrin

Keywords

  • Asymmetric synthesis
  • Chemical biology
  • Natural products
  • Panepophenanthrin
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enantio- and diastereoselective total synthesis of (+)-panepophenanthrin, a ubiquitin-activating enzyme inhibitor, and biological properties of its new derivatives. / Matsuzawa, Masayoshi; Kakeya, Hideaki; Yamaguchi, Junichiro; Shoji, Mitsuru; Onose, Rie; Osada, Hiroyuki; Hayashi, Yujiro.

In: Chemistry - An Asian Journal, Vol. 1, No. 6, 2006, p. 845-851.

Research output: Contribution to journalArticle

Matsuzawa, Masayoshi ; Kakeya, Hideaki ; Yamaguchi, Junichiro ; Shoji, Mitsuru ; Onose, Rie ; Osada, Hiroyuki ; Hayashi, Yujiro. / Enantio- and diastereoselective total synthesis of (+)-panepophenanthrin, a ubiquitin-activating enzyme inhibitor, and biological properties of its new derivatives. In: Chemistry - An Asian Journal. 2006 ; Vol. 1, No. 6. pp. 845-851.
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