6‐Deoxyhexoses from l‐Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology |
| |
| Authors: | Dr Zilei Liu Prof Dr Akihide Yoshihara Dr Ciarán Kelly Dr John T Heap Mikkel H S Marqvorsen Dr Sarah F Jenkinson Dr Mark R Wormald Dr José M Otero Dr Amalia Estévez Prof Dr Atsushi Kato Prof Dr George W J Fleet Prof Dr Ramón J Estévez Prof Dr Ken Izumori |
| |
| Institution: | 1. Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK;2. Glycobiology Institute, Department of Biochemistry, University of Oxford, Oxford, UK;3. International Institute of Rare Sugar Research and Education, Kagawa University, Kagawa, Japan;4. Centre for Synthetic Biology and Innovation, Department of Life Sciences, Imperial College, London, UK;5. Departamento de Química Orgánica and Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares, Universidade de Santiago de Compostela, Santiago de Compostela, Spain;6. Department of Hospital Pharmacy, University of Toyama, Toyama, Japan |
| |
| 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. |
| |
| Keywords: | 6-deoxyhexoses carbohydrates gene expression rhamnonolactone rhamnose operon |
|
|
