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 Heap, Mikkel Marqvorsen, Sarah Jenkinson, Mark Wormald, Jose Otero, Amalia Estévez, Atsushi Kato, George Fleet, Ramón Estévez, Ken Izumori

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)
15 Downloads (Pure)

Abstract

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.
Original languageEnglish
Pages (from-to)12557-12565
JournalChemistry - A European Journal
Volume22
Issue number35
Early online date21 Jul 2016
DOIs
Publication statusPublished - 22 Aug 2016
Externally publishedYes

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