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6‐Deoxyhexoses from l‐Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology
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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 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(35):12557-12565
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. 相似文献
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