Preparation and Biological Evaluation of Pyrrolidinediols and Pyrrolidine N-Oxides from D-Ribose Using the Nitrone Approach

Palmer, Andreas Marc; Jäger, Volker

doi:10.1002/1099-0690(200107)2001:13<2547::aid-ejoc2547>3.0.co;2-h

Cited by 26 publications

(12 citation statements)

References 19 publications

(35 reference statements)

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“…Applying simple transformations to these pyrrolidine N-oxides, a variety of iminopolyols with glycosidase-inhibiting properties is available (to be described in detail in the following paper of this series). [40] Experimental Section General Remarks: Melting points were determined on a FisherϪJohns 4017 heating block and are uncorrected. Ϫ 1 H and 13 C NMR spectra were recorded with Bruker AC 250, ARX 300, ARX 500 spectrometers using Me 4 Si as internal standard.…”

Section: Resultsmentioning

confidence: 63%

“…In all such cases, structures were confirmed by HRMS; in many cases, transformations of these hygroscopic pyrrolidine N-oxides were performed to yield products with correct analyses. [40] …”

Section: Resultsmentioning

confidence: 99%

“…Transformation of selected products to the parent 2-or 2,5-(di)substituted dihydroxypyrrolidines along with results of the biological evaluation, mainly concerning fucosidase inhibition, are reported in the next paper of this series. [40] Results and Discussion…”

Section: Copeϫhouse Cyclization Of Unsaturated Hydroxylaminesmentioning

confidence: 99%

“…A variety of reagents was used in order to explore structureϪactivity relationships with regard to the intended tests of fucosidase inhibition. [40] As indicated in Table 1, most additions occurred readily at low temperatures, typically requiring 2 to 8 h for completion. The cyclization of the intermediate hydroxylamines 9 and 10 was then carried out in chloroform as above; this had been described as the optimum solvent for the CopeϪHouse cyclization.…”

Section: Nucleophilic Addition Of Hydride and Grignard Reagents To Nimentioning

confidence: 99%

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PyrrolidineN-Oxides by Stereoselective Addition of Grignard and Lithium Compounds to 4,5-Dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenoseN-Benzyl Nitrone and Subsequent Cope−House Cyclization

Palmer

Jäger

2001

Eur. J. Org. Chem.

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Section: Resultsmentioning

confidence: 63%

Section: Resultsmentioning

confidence: 99%

Section: Copeϫhouse Cyclization Of Unsaturated Hydroxylaminesmentioning

confidence: 99%

Section: Nucleophilic Addition Of Hydride and Grignard Reagents To Nimentioning

confidence: 99%

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PyrrolidineN-Oxides by Stereoselective Addition of Grignard and Lithium Compounds to 4,5-Dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenoseN-Benzyl Nitrone and Subsequent Cope−House Cyclization

Palmer

Jäger

2001

Eur. J. Org. Chem.

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“…The inhibitory activity of 64 towardsgalactosidase and -mannosidase is quite similar to that of A powerful inhibitior 85 against -fucosidase is similar to that of compound 63 [77,104]. Compounds with (2R,3R,4S)-configuration (86)(87)(88)(89)(90)(91)(92)(93)(94)(95)(96)(97) showed moderate inhibitory activities against -mannosidase [89], and those with a (2R,3S,4R)-configuration (98)(99)(100)(101)(102)(103)(104)(105)(106)(107)(108)(109) tend to inhibitglucosidase and -galactosidase [88,89,93,109,110]. The specificity of these compounds was explained based on the similarity with substrate structures of individual enzymes where it was considered that a flexible pyrrolidine structure could adopt a 4 E conformation and 2-and 3-OH groups might mimic the hydroxyl groups of glucopyranosyl cation species (Fig.…”

Section: Cis-diol (B-type) [64777899102-108]mentioning

confidence: 99%

3,4-Dihydroxypyrrolidine as Glycosidase Inhibitor

Suzuki

Nakahara²,

Kanie³

2009

CTMC

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Glycosidases are involved in various important biological processes including digestion of starch in the intestine, oligosaccharide processing inside rough ER and Golgi apparatus, and degradation of glycoconjugates in lysosomes. It is apparent that inhibitors of this class of enzymes are useful in the investigation of biological functions of glycoconjugates. Furthermore, it is believed that these compounds are important as pharmaceuticals. The structures of glycosidase inhibitors can be categorized into two major classes; ground-state mimetics and transition-state mimetics. The former has a chair-shaped six-membered structure that mimics monosaccharides where ring oxygens are often replaced with other elements for an improved binding affinity. On the other hand, the latter possesses a somewhat distorted shape compared with the chair conformation of carbohydrates. One of the ways to derive such distortion is by the introduction of sp2 character into the six-membered ring, and another is by ring contraction to form a five-membered system for the transition-state mimetics. The functions of these transition-state mimetics are often unpredictable regarding inhibitory activity and enzyme specificity. This review focuses on such "difficult to predict" species in an attempt to extract information or common aspects for the future development of inhibitors of glycosidases based on transition-state mimetics.

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Stereoselective Aldol Additions Catalyzed by Dihydroxyacetone Phosphate‐Dependent Aldolases in Emulsion Systems: Preparation and Structural Characterization of Linear and Cyclic Iminopolyols from Aminoaldehydes

Espelt

Parella

Bujons³

et al. 2003

Chemistry A European J

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The potential of dihydroxyacetone phosphate (DHAP)-dependent aldolases to catalyze stereoselective aldol additions is, in many instances, limited by the solubility of the acceptor aldehyde in aqueous/co-solvent mixtures. Herein, we demonstrate the efficiency of emulsion systems as reaction media for the class I fructose-1,6-bisphosphate aldolase (RAMA) and class II recombinant rhamnulose-1-phosphate aldolase from E. coli (RhuA)-catalyzed aldol addition between DHAP and N-benzyloxycarbonyl (N-Cbz) aminoaldehydes. The use of emulsions improved the RAMA-catalyzed aldol conversions by three to tenfold relative to those in conventional DMF/water mixtures. RhuA was more reactive than RAMA towards the N-Cbz aminoaldehydes regardless of the reaction medium. With (S)- or (R)-Cbz-alaninal, RAMA exhibited preference for the R enantiomer, while RhuA had no enantiomeric discrimination. The linear N-Cbz aminopolyols thus obtained were submitted to catalytic intramolecular reductive amination to afford the corresponding iminocyclitols. This reaction was diastereoselective in all cases examined; the face selectivity was controlled by the stereochemistry of the newly formed hydroxyl group originating from the aldehyde. Characterization of the resulting iminocyclitols allowed the assessment of the diastereoselectivity of the enzymatic aldol reactions with respect to the N-protected aminoaldehyde. RAMA formed single diastereoisomers from N-Cbz-glycinal and from both enantiomers of N-Cbz-alaninal, while 14 % of the epimeric product was observed from N-Cbz-3-aminopropanal. Diastereoselectivity from RhuA was lower than that observed from RAMA. Interestingly, a single diastereoisomer was formed from (S)-Cbz-alaninal, whereas only a 34 % diastereomeric excess was observed from its enantiomer (i.e., (R)-Cbz-alaninal).

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Preparation and Biological Evaluation of Pyrrolidinediols and Pyrrolidine N-Oxides from D-Ribose Using the Nitrone Approach

Cited by 26 publications

References 19 publications

PyrrolidineN-Oxides by Stereoselective Addition of Grignard and Lithium Compounds to 4,5-Dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenoseN-Benzyl Nitrone and Subsequent Cope−House Cyclization

PyrrolidineN-Oxides by Stereoselective Addition of Grignard and Lithium Compounds to 4,5-Dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenoseN-Benzyl Nitrone and Subsequent Cope−House Cyclization

3,4-Dihydroxypyrrolidine as Glycosidase Inhibitor

Stereoselective Aldol Additions Catalyzed by Dihydroxyacetone Phosphate‐Dependent Aldolases in Emulsion Systems: Preparation and Structural Characterization of Linear and Cyclic Iminopolyols from Aminoaldehydes

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