6-Deoxyhexoses from l-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology

Zilei Liu, Akihide Yoshihara*, Ciarán Kelly, John T. Heap, Mikkel H.S. Marqvorsen, Sarah F. Jenkinson, Mark R. Wormald, José M. Otero, Amalia Estévez, Atsushi Kato, George W.J. Fleet, Ramón J. Estévez, Ken Izumori

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

8 被引用数 (Scopus)

抄録

In the search for alternative non-metabolizable inducers in the l-rhamnose promoter system, the synthesis of fifteen 6-deoxyhexoses from l-rhamnose demonstrates the value of synergy between biotechnology and chemistry. The readily available 2,3-acetonide of rhamnonolactone allows inversion of configuration at C4 and/or C5 of rhamnose to give 6-deoxy-d-allose, 6-deoxy-d-gulose and 6-deoxy-l-talose. Highly crystalline 3,5-benzylidene rhamnonolactone gives easy access to l-quinovose (6-deoxy-l-glucose), l-olivose and rhamnose analogue with C2 azido, amino and acetamido substituents. Electrophilic fluorination of rhamnal gives a mixture of 2-deoxy-2-fluoro-l-rhamnose and 2-deoxy-2-fluoro-l-quinovose. Biotechnology provides access to 6-deoxy-l-altrose and 1-deoxy-l-fructose.

本文言語英語
ページ(範囲)12557-12565
ページ数9
ジャーナルChemistry - A European Journal
22
35
DOI
出版ステータス出版済み - 2016/08/22

ASJC Scopus 主題領域

  • 触媒
  • 化学一般
  • 有機化学

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