322726-64-7Relevant academic research and scientific papers
6-Deoxyhexoses from l-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology
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
, p. 12557 - 12565 (2016)
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.
Two epimerisations in the formation of oxetanes from L-rhamnose: Towards oxetane-containing peptidomimetics
Johnson, Stephen W.,Angus, Donald,Taillefumier, Claude,Jones, John H.,Watkin, David J.,Floyd, Emma,Buchanan,Fleet, George W.J.
, p. 4113 - 4125 (2007/10/03)
The methyl group in (R)-3,5-O-benzylidene-L-rhamnono-1,4-lactone 2, prepared from L-rhamnose 1 in 41% yield without need for chromatography, is axial and provides a good example of Mills' rule that the 'O-inside' conformations are, in general, more stable than alternative 'H-inside' conformations. The lactone 2 may be converted in two steps in an overall 57% yield to the rhamnono-oxetane 3, which should be useful in generating oxetane dipeptide isosteres and oxetane β-amino acids and in determining the value of the oxetane ring in inducing secondary structure in small peptidomimetics. Methyl 2,4-anhydro-(S)-3,5-O-benzylidene-L-rhamnonate 11, in which both the phenyl and methyl groups are equatorial, is slightly more thermodynamically stable than 3, providing a rare exception to Mills' rule. X-ray crystal structures of 2 and 11 are reported. Copyright (C) 2000 Elsevier Science Ltd.
