Synthesis and Chemistry of Noeuromycin and Isofagomine Analogues

Liu, Huizhen; Lillelund, Vinni H.; Andersch, Jens; Liang, Xifu; Bols, Mikael

doi:10.1081/car-200030070

Cited by 11 publications

(7 citation statements)

References 10 publications

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“…The dehydration might have occurred through an iminium cation, according to the facile dehydration reported for the hemiaminal moiety in aza-sugars. [30] The proton vicinal coupling constants of 7a-h (J 2,3 = 9.2-9.4, J 3,4a = 9.2-9.4 Hz) are in agreement with a half-chair conformation 3 H 2 (Table 3).…”

Section: Entrymentioning

confidence: 51%

1‐Alkoxyamino‐2‐nitroalkanes as Key Building Blocks for a Chemo‐ and Diastereoselective Synthesis of a New Type of Polyfunctionalized N‐Alkoxypiperidine

et al. 2010

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A highly efficient conversion of β-nitrostyrenes into a new kind of functionalized N-alkoxy-2-hydroxypiperidine in two steps was developed, giving excellent yields and diastereoselectivity. The prepared compounds are the first examples of N-alkoxy-2-hydroxypiperidines. The synthetic approach involved the conjugate addition of alkoxyamines to β-nitrostyrenes, followed by Michael addition of the isolated nitro-

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Section: Entrymentioning

confidence: 51%

1‐Alkoxyamino‐2‐nitroalkanes as Key Building Blocks for a Chemo‐ and Diastereoselective Synthesis of a New Type of Polyfunctionalized N‐Alkoxypiperidine

et al. 2010

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“…The encouraging glycosidase inhibition results obtained with 1,6-dideoxy-1,6-iminoheptitols forced us to look at another canonical glycosidase inhibitor, noeuromycin, a nanomolar -glucosidase inhibitor designed by Bols to mimic the carbocationic form of the glycosyl oxocarbenium ion-like transition state in which the positive charge is located on the anomeric carbon. 70 As noeuromycin has been reported to undergo the Amadori rearrangement depending on pH, 71 we thought that generating chemically more stable ring homologues of this molecule could be worthy of a trial ( Figure 6). To access these derivatives, we developed a strategy exploiting a sugar-derived 6-azidolactol 23 available in 6 steps from commercial tetra-O-benzyl D-glucopyranose.…”

Section: Noeuromycin Ring Homologuesmentioning

confidence: 99%

Contributing to the Study of Enzymatic and Chemical Glycosyl Transfer Through the Observation and Mimicry of Glycosyl Cations

Blériot¹

2020

Synthesis

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This account describes our efforts dedicated to: 1) the design of glycomimetics aimed at targeting therapeutically relevant carbohydrate processing enzymes, and 2) the observation, characterization, and exploitation of glycosyl cations as a tool for studying the glycosylation reaction. These findings have brought important data regarding this key ionic species as well as innovative strategies to access iminosugars of interest.1 Introduction2 The Glycosyl Cation, A Central Species in Glycosciences2.1 A Selection of the Strategies Developed so far to Gain Insights into Glycosyl Cations Structure2.2 When Superacids Meet Carbohydrates3 Chemical Probes to Gain Insights into the Pseudorotational Itinerary of Glycosides During Glycosidic Bond Hydrolysis3.1 Conformationally Locked Glycosides3.1.1 The Xylopyranose Case3.1.2 The Mannopyranose Case3.2 Conformationally Flexible Iminosugars3.2.1 Nojirimycin Ring Homologues3.2.2 Noeuromycin Ring Homologues3.2.3 Seven-Membered Iminosugar C-Glycosides4 N-Acetyl-d-glucosamine Mimics5 Ring Contraction: A Useful Tool to Increase Iminosugar’s Structural Diversity6 Regioselective Deprotection of Iminosugar C-Glycosides to Introduce Diversity at C2 Position7 Conclusion

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“…10 This compound proved to be unstable at neutral pH and rearrange to the corresponding hydrated ketone due to the labile hemiaminal moiety. 11 Concomitantly, the group of Nishimura disclosed the synthesis and biological evaluation of gem-diamine 1-N-iminosugars which display glycosidase inhibition potencies similar to isofagomine 12 but which proved also unstable during enzymatic assays. 13 To circumvent this problem, Schuster 14 and Noort et al 15 designed some piperidine-based 1-N-iminosugars with homologated 2-OH or 2-NHAc groups, respectively.…”

Section: Introductionmentioning

confidence: 99%

Conformational analysis of seven-membered 1-N-iminosugars by NMR and molecular modelling

et al. 2012

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International audienceThe conformational analysis of a series of tri- and tetrahydroxyazepanes 1-6 designed as noeuromycin mimics has been carried out using H-1 NMR spectroscopy assisted by molecular mechanics, molecular dynamics and Monte Carlo calculations. A marked flexibility for these compounds has been found. Superimposition of the branched azepanes with known glycosidase inhibitors (DMJ, DNJ, IFG and noeuromycin) was in accordance with the glycosidase inhibition profile of the polyhydroxylated azepanes. Additional STD experiments confirmed the potency and competitive character of azepane 3 towards almond beta-glucosidase

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Synthesis and Chemistry of Noeuromycin and Isofagomine Analogues

Cited by 11 publications

References 10 publications

1‐Alkoxyamino‐2‐nitroalkanes as Key Building Blocks for a Chemo‐ and Diastereoselective Synthesis of a New Type of Polyfunctionalized N‐Alkoxypiperidine

1‐Alkoxyamino‐2‐nitroalkanes as Key Building Blocks for a Chemo‐ and Diastereoselective Synthesis of a New Type of Polyfunctionalized N‐Alkoxypiperidine

Contributing to the Study of Enzymatic and Chemical Glycosyl Transfer Through the Observation and Mimicry of Glycosyl Cations

Conformational analysis of seven-membered 1-N-iminosugars by NMR and molecular modelling

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