6-deoxyhexoses from L-rhamnose in the search for inducers of the rhamnose operon: Synergy of chemistry and biotechnology

Journal article

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.

Authors: Liu, Z; Wormald, M; Yoshihara, A; Kelly, C; Heap, J

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Wiley
• Journal: Chemistry - A European Journal
• Volume: 22
• Issue: 35
• Pages: 12557–12565
• Publication date: 2016-07-01
• Acceptance date: 2016-06-21
• DOI: 10.1002/chem.201602482
• Keywords: rare sugar; rhamnonolactone; rhamnose operon; 6-deoxyhexose