A synthetic approach to aromatic aminoglycoside as a neamine mimic

Ryo Inoue, Sho Matsuda, Yoshiki Oda, Hirofumi Ooyama, Akihiro Yoshida, Keita Hamasaki, Takashi Yamanoi

Research output: Contribution to journalArticle

Abstract

This paper describes the synthetic approach to an aromatic a-glycoside as a mimic of neamine, which is a common core structure of some aminoglycoside antibiotics. We achieved the synthesis of the protected precursor of the neamine mimic, 4-(2,6-diamino-2,6-dideoxy-α-D-glucopyranosyloxy)-1,3- phenylenediamine, from N-acetyl-D-glucosamine and 2,4-diaminophenol as the starting materials using a glycosylation technique.

Original languageEnglish
Pages (from-to)1335-1343
Number of pages9
JournalHeterocycles
Volume84
Issue number2
DOIs
Publication statusPublished - 2012

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2,4-diaminophenol
Aminoglycosides
Glycosylation
Acetylglucosamine
Glycosides
Anti-Bacterial Agents
neamine
3-phenylenediamine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Inoue, R., Matsuda, S., Oda, Y., Ooyama, H., Yoshida, A., Hamasaki, K., & Yamanoi, T. (2012). A synthetic approach to aromatic aminoglycoside as a neamine mimic. Heterocycles, 84(2), 1335-1343. https://doi.org/10.3987/COM-11-S(P)69

A synthetic approach to aromatic aminoglycoside as a neamine mimic. / Inoue, Ryo; Matsuda, Sho; Oda, Yoshiki; Ooyama, Hirofumi; Yoshida, Akihiro; Hamasaki, Keita; Yamanoi, Takashi.

In: Heterocycles, Vol. 84, No. 2, 2012, p. 1335-1343.

Research output: Contribution to journalArticle

Inoue, R, Matsuda, S, Oda, Y, Ooyama, H, Yoshida, A, Hamasaki, K & Yamanoi, T 2012, 'A synthetic approach to aromatic aminoglycoside as a neamine mimic', Heterocycles, vol. 84, no. 2, pp. 1335-1343. https://doi.org/10.3987/COM-11-S(P)69
Inoue, Ryo ; Matsuda, Sho ; Oda, Yoshiki ; Ooyama, Hirofumi ; Yoshida, Akihiro ; Hamasaki, Keita ; Yamanoi, Takashi. / A synthetic approach to aromatic aminoglycoside as a neamine mimic. In: Heterocycles. 2012 ; Vol. 84, No. 2. pp. 1335-1343.
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