Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ.
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An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic & thermodynamic azido-γ-lactones.
Org Biomol Chem
September 2013
Oxford Glycobiology Institute, University of Oxford, South Parks Road, Oxford, OX1 3QU, UK.
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.
View Article and Find Full Text PDFStereodivergent synthesis of iminosugars from stannylated derivatives of (S)-vinylglycinol.
Org Lett
January 2013
Université de Nantes CNRS, CEISAM, UMR 6230, Faculté des Sciences et des Techniques, 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3 France.
An original access to iminosugars from a cis/trans mixture of stannylated oxazolidinones 5 is reported. The dehydropiperidines 7-trans and 7-cis were obtained stereoselectively with an RS and SS configuration depending on the order of the Sn-Li transmetalation (followed by electrophilic trapping) and of the ring closing metathesis reactions due to the stereoselective epimerization of the α-aminoanion intermediate. The dehydropiperidines 7-trans and 7-cis were subsequently used for the synthesis of enantiopure homonojirimycin analogs.
View Article and Find Full Text PDFEight stereoisomers of homonojirimycin from D-mannose.
Org Lett
April 2012
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, OX1 3TA, UK.
Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ.
View Article and Find Full Text PDFConvergent approach toward the synthesis of the stereoisomers of C-6 homologues of 1-deoxynojirimycin and their analogues: evaluation as specific glycosidase inhibitors.
J Org Chem
October 2006
Division of Organic Chemistry (Synthesis) and Division of Biochemical Science, National Chemical Laboratory, Pune-411008, India.
A new and stereoselective strategy is developed to synthesize an appropriate template 9 to obtain C-6 homologues of 1-deoxyazasugars such as 1-deoxy-D-galactohomonojirimycin (5), 1-deoxy-4-hydroxymethyl-D-glucohomonojirimycin (6), and their enantiomers. The template 9 is also used to obtain neutral nonbasic pseudo-glyconolactam (8), C-4 amino, and methyl analogues of 1-deoxy-homonojirimycin as new analogues of 1-deoxyhomoazasugars. Compound 5 is found to be a potent and specific inhibitor to alpha-galactosidase (Ki = 1.
View Article and Find Full Text PDFIminosugar-producing Thai medicinal plants.
J Nat Prod
August 2005
Faculty of Pharmaceutical Sciences, Hokuriku University, Ho-3 Kanagawa-machi, Kanazawa 920-1181, Japan.
Alpha-1-C-hydroxymethylfagomine (7), 3-O-beta-D-glucopyranosyl-DMDP (12), and 2,5-dideoxy-2,5-imino-D-glucitol (13) were isolated from the Thai traditional crude drug "Non tai yak" (Stemona tuberosa), which also contains a high concentration level of alpha-homonojirimycin (0.1% dry weight). "Thopthaep" (Connarus ferrugineus) and "Cha em thai" (Albizia myriophylla) contained 1-deoxymannojirimycin (DMJ) (10) at levels of 0.
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