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@article{Liu:2016:10.1002/chem.201602482,
author = {Liu, Z and Yoshihara, A and Kelly, C and Heap, JT and Marqvorsen, MH and Jenkinson, SF and Wormald, MR and Otero, JM and Estévez, A and Kato, A and Fleet, GW and Estévez, RJ and Izumori, K},
doi = {10.1002/chem.201602482},
journal = {Chemistry},
pages = {12557--12565},
title = {6-Deoxyhexoses from l-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology},
url = {http://dx.doi.org/10.1002/chem.201602482},
volume = {22},
year = {2016}
}

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TY  - JOUR
AB  - 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.
AU  - Liu,Z
AU  - Yoshihara,A
AU  - Kelly,C
AU  - Heap,JT
AU  - Marqvorsen,MH
AU  - Jenkinson,SF
AU  - Wormald,MR
AU  - Otero,JM
AU  - Estévez,A
AU  - Kato,A
AU  - Fleet,GW
AU  - Estévez,RJ
AU  - Izumori,K
DO  - 10.1002/chem.201602482
EP  - 12565
PY  - 2016///
SN  - 1521-3765
SP  - 12557
TI  - 6-Deoxyhexoses from l-Rhamnose in the Search for Inducers of the Rhamnose Operon: Synergy of Chemistry and Biotechnology
T2  - Chemistry
UR  - http://dx.doi.org/10.1002/chem.201602482
UR  - http://hdl.handle.net/10044/1/38665
VL  - 22
ER  -

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