6-Deoxyhexoses from l-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology
File(s)
Accepted version
Author(s)
Type
Journal Article
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.
Date Issued
2016-07-21
Date Acceptance
2016-07-01
Citation
Chemistry, 2016, 22 (35), pp.12557-12565
ISSN
1521-3765
Publisher
Wiley
Start Page
12557
End Page
12565
Journal / Book Title
Chemistry
Volume
22
Issue
35
Copyright Statement
This is the peer reviewed version of the following article: Liu, Z., Yoshihara, A., Kelly, C., Heap, J. T., Marqvorsen, M. H. S., Jenkinson, S. F., Wormald, M. R., Otero, J. M., Estévez, A., Kato, A., Fleet, G. W. J., Estévez, R. J. and Izumori, K. (2016), 6-Deoxyhexoses from l-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology. Chem. Eur. J., which has been published in final form at https://dx.doi.org/10.1002/chem.201602482. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
Sponsor
Biotechnology and Biological Sciences Research Council (BBSRC)
Grant Number
BB/M011321/1
Subjects
6-deoxyhexoses
carbohydrates
gene expression
rhamnonolactone
rhamnose operon
General Chemistry
03 Chemical Sciences
Publication Status
Published