An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones

Andreas F.G. Glawar; Sarah F. Jenkinson; Scott J. Newberry; Amber L. Thompson; Shinpei Nakagawa; Akihide Yoshihara; Kazuya Akimitsu; Ken Izumori; Terry D. Butters; Atsushi Kato; George W.J. Fleet

doi:10.1039/c3ob41334a

An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones

Andreas F.G. Glawar, Sarah F. Jenkinson, Scott J. Newberry, Amber L. Thompson, Shinpei Nakagawa, Akihide Yoshihara, Kazuya Akimitsu, Ken Izumori, Terry D. Butters, Atsushi Kato^*, George W.J. Fleet

^*Corresponding author for this work

Hospital Pharmacy

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d- ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d- glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented.

Original language	English
Pages (from-to)	6886-6899
Number of pages	14
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	40
DOIs	https://doi.org/10.1039/c3ob41334a
State	Published - 2013/10/28

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Glawar, A. F. G., Jenkinson, S. F., Newberry, S. J., Thompson, A. L., Nakagawa, S., Yoshihara, A., Akimitsu, K., Izumori, K., Butters, T. D., Kato, A., & Fleet, G. W. J. (2013). An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones. Organic and Biomolecular Chemistry, 11(40), 6886-6899. https://doi.org/10.1039/c3ob41334a

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title = "An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones",

abstract = "Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d- ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d- glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented.",

author = "Glawar, {Andreas F.G.} and Jenkinson, {Sarah F.} and Newberry, {Scott J.} and Thompson, {Amber L.} and Shinpei Nakagawa and Akihide Yoshihara and Kazuya Akimitsu and Ken Izumori and Butters, {Terry D.} and Atsushi Kato and Fleet, {George W.J.}",

year = "2013",

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doi = "10.1039/c3ob41334a",

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volume = "11",

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journal = "Organic and Biomolecular Chemistry",

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T1 - An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones

AU - Glawar, Andreas F.G.

AU - Jenkinson, Sarah F.

AU - Newberry, Scott J.

AU - Thompson, Amber L.

AU - Nakagawa, Shinpei

AU - Yoshihara, Akihide

AU - Akimitsu, Kazuya

AU - Izumori, Ken

AU - Butters, Terry D.

AU - Kato, Atsushi

AU - Fleet, George W.J.

PY - 2013/10/28

Y1 - 2013/10/28

N2 - Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d- ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d- glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented.

AB - Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d- ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d- glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented.

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U2 - 10.1039/c3ob41334a

DO - 10.1039/c3ob41334a

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An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones

Abstract

ASJC Scopus subject areas

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