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6‐Deoxyhexoses from l ‐Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology
Author(s) -
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.,
Izumori Ken
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602482
Subject(s) - rhamnose , operon , inducer , chemistry , stereochemistry , biochemistry , polysaccharide , gene , escherichia coli
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.