Diverse Synthesis of Natural Trehalosamines and Synthetic 1,1′-Disaccharide Aminoglycosides

Yen Chu Lu, Soumik Mondal, Ching Chi Wang, Chun Hung Lin, Kwok-Kong Mong*

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Scopus citations

Abstract

A general strategy for the diverse synthesis of ten disaccharide aminoglycosides, including natural 2-trehalosamine (1), 3-trehalosamine (2), 4-trehalosamine (3), and neotrehalosyl 3,3′-diamine (8) and synthetic aminoglycosides 4–7, 9, and 10, has been developed. The aminoglycoside compounds feature different anomeric configurations and numbers of amino groups. The key step for the synthesis was the glycosylation coupling of a stereodirecting donor with a configuration-stable TMS glycoside acceptor. Either the donor or acceptor could be substituted with an azido group. The aminoglycosides prepared in the present study were characterized by 1D and 2D NMR spectroscopy.

Original languageEnglish
Pages (from-to)287-294
Number of pages8
JournalChemBioChem
Volume20
Issue number2
DOIs
StatePublished - 18 Jan 2019

Keywords

  • aminoglycosides
  • disaccharides
  • glycosylation
  • protecting groups
  • trimethylsilyl glycoside acceptors

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