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6-deoxyhexoses from L-rhamnose in the search for inducers of the rhamnose operon: Synergy of chemistry and biotechnology

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-g...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1002/chem.201602482

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Institution:
University of Oxford
Department:
Oxford, MSD, Biochemistry
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Institution:
University of Oxford
Department:
Oxford, MSD, Biochemistry
Yoshihara, A More by this author
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Funding agency for:
Fleet, GWJ
Publisher:
Wiley Publisher's website
Journal:
Chemistry - A European Journal Journal website
Volume:
22
Issue:
35
Pages:
12557–12565
Publication date:
2016-07-05
Acceptance date:
2016-06-21
DOI:
URN:
uuid:9a03fc97-01ae-4c72-af6a-9393e5116b48
Source identifiers:
631798
Local pid:
pubs:631798

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