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6-Deoxyhexoses froml-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology
- Publication Year :
- 2016
- Publisher :
- Wiley-Blackwell, 2016.
-
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.
- 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
Subjects
Details
- Language :
- English
- ISSN :
- 09476539
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....ef8a31bedb1719191b777a7292ef32c9