Biocatalytic Synthesis of Non-Natural Monoterpene O-Glycosides Exhibiting Superior Antibacterial and Antinematodal Properties

A promiscuous Bacillus glycosyltransferase (YjiC) was explored for the enzymatic synthesis of monoterpene O-glycosides in vitro and in vivo. YjiC converted seven monoterpenes into 41 different sugar-conjugated novel glycoside derivatives. The whole-cell biotransformation of the same set of monoterpenes exhibited robust enzyme activity to synthesize O-glucosyl derivatives from Escherichia coli. These newly synthesized selected monoterpene-O-glucosyl derivatives exhibited enhanced antibacterial activities against human pathogenic bacteria and antinematodal activities against pine wood nematode Bursaphelenchus xylophilus.

• Publication year

  2019

• Venue

  ACS Omega

• Publication date

  2019-05-29

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  DOI 10.1021/acsomega.9b00535PMID 31460026PMCID 6648847
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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  2008influential reference
• Management of acute organophosphorus pesticide poisoning

  2008cited by this paper
• Natural-product sugar biosynthesis and enzymatic glycodiversification.

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  2001cited by this paper
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  2000cited by this paper
• The role of carbohydrates in biologically active natural products.

  1997cited by this paper
• Biotransformation of isoeugenol and eugenol by cultured cells of Eucalyptus perriniana.

  1992cited by this paper

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