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An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones
- Publication Year :
- 2016
-
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.
- Subjects :
- chemistry.chemical_classification
Models, Molecular
Azides
1-Deoxynojirimycin
Stereochemistry
Organic Chemistry
Molecular Conformation
Stereoisomerism
Crystal structure
Biochemistry
Reductive amination
Amino acid
chemistry.chemical_compound
Kinetics
Lactones
Glucose
chemistry
D-Glucose
Organic chemistry
Thermodynamics
Glycoside hydrolase
Stereoselectivity
Azide
Physical and Theoretical Chemistry
Trifluoromethanesulfonate
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....328ec3a7562e37e2f271e97260e00ed6