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2 results on '"rhamnose operon"'

1. 6-Deoxyhexoses from l-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology.

Author

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

Subjects
*RHAMNOSE, *OPERONS, *FLUORINATION, *BIOTECHNOLOGY, *ELECTROPHILES
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. [ABSTRACT FROM AUTHOR]

Published
2016
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2. 6-Deoxyhexoses froml-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology

Author

José M. Otero, Sarah F. Jenkinson, Amalia M. Estévez, Akihide Yoshihara, Ciarán L. Kelly, Mikkel H. S. Marqvorsen, Atsushi Kato, Mark R. Wormald, Zilei Liu, Ramón J. Estévez, John T. Heap, George W. J. Fleet, Ken Izumori, and Biotechnology and Biological Sciences Research Council (BBSRC)

Subjects
Rhamnose, Operon, Stereochemistry, F100, carbohydrates, Fructose, Deoxyglucose, rhamnose operon, 010402 general chemistry, rhamnonolactone, 01 natural sciences, Catalysis, chemistry.chemical_compound, General chemistry, Deoxy Sugars, Inducer, Hexoses, 010405 organic chemistry, business.industry, Organic Chemistry, Electrophilic fluorination, General Chemistry, C700, 0104 chemical sciences, Biotechnology, Glucose, 6-deoxyhexoses, chemistry, gene expression, business, 03 Chemical Sciences
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.

Published
2016

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