135395-58-3Relevant academic research and scientific papers
Inhibition of naringinase (L-rhamnosidase) by piperidine analogues of L-rhamnose: Scaffolds for libraries incorporating trihydroxypipecolic acids
Shilvock, John P.,Wheatley, Joseph R.,Davis, Benjamin,Nash, Robert J.,Griffiths, Rhodri C.,Jones, M. George,Mueller, Matthias,Crook, Sarah,Watkin, David J.,Smith, Colin,Besra, Gurdyal S.,Brennan, Patrick J.,Fleet, George W.J.
, p. 8569 - 8572 (1996)
L-Deoxyrhamnojirimycin 1 does not inhibit naringinase significantly but 5-epi-L-deoxyrhamnojirimycin 2 is a potent inhibitor. Conversely, α-C-glycosides of 1 are good inhibitors of L-rhamnosidase whereas those of 2 are not. Intermediate azabicyclic lactones are likely to be of use for the incorporation of a number of trihydrocypipecolic acids into peptide libraries.
Synthesis of 1,6-dideoxynojirimycin, 1,6-dideoxy-D-allo-nojirimycin, and 1,6-dideoxy-D-gulo-nojirimycin via asymmetric hetero-Diels-Alder reactions
Defoin,Sarazin,Streith
, p. 560 - 567 (1996)
Asymmetric Diels-Alder reaction of sorbaldehyde O-methyloxime 1d with chiral chloronitroso derivative 2 of D-mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%). Catalytic hydrogenolysis
5-epi-Deoxyrhamnojirimycin is a potent inhibitor of an α-L- rhamnosidase: 5-epi-Deoxymannojirimycin is not a potent inhibitor of an α- D-mannosidase
Davis, Benjamin G.,Hull, Andrew,Smith, Colin,Nash, Robert J.,Watson, Alison A.,Winkler, David A.,Griffiths, Rhodri C.,Fleet, George W. J.
, p. 2947 - 2960 (2007/10/03)
Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an α-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an α-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L- rhamnose which are recognised by enzymes that synthesise or process L- rhamnose may inhibit either the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-5 epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the 4H3 conformation of the relevant glycopyranosyl cation intermediate.
6-Deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, D-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions
Defoin, Albert,Sarazin, Herve,Streith, Jacques
, p. 13783 - 13796 (2007/10/03)
Nucleophilic ring opening of the cyclic sulfates (±)-9c and D-9c and of the epoxide (±)-13, or double substitution of the bis-triflate D-10 (derived from the Diels-Alder adduct of hexodienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy-nojirimycin and its isomers are mixtures of α- and β-anomers and of the corresponding imine.
Fluorinated 1,5-Dideoxy-1,5-iminoalditols: Synthesis of 1,5,6-Trideoxy-6-fluoro-1,5-imino-D-glucitol (1,6-Dideoxy-6-fluoronojirimycin) and 1,4,5-Trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-Trideoxy-2-fluoro-1,5-imino-L-ribitol)
Di, Jie,Rajanikanth, Bandaru,Szarek, Walter A.
, p. 2151 - 2154 (2007/10/02)
An efficient synthesis of 1,5,6-trideoxy-6-fluoro-1,5-imino-D-glucitol 13 from inexpensive L-sorbose by way of reductive amination of 12 is described.Synthesis of 1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-trideoxy-2-fluoro-1,5-imino-L-ribitol) 19
