Iron(iii) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides

Bourdreux, Yann; Lemétais, Aurélie; Urban, Dominique; Beau, Jean‐Marie

doi:10.1039/c0cc04398b

Cited by 78 publications

(59 citation statements)

References 38 publications

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“…However, mesenchymal stem cells have been found to significantly contribute in the wound healing process post-MI 14 . Previous studies have shown that myofibroblasts may originate from several sources, including expansion of resident fibroblasts, hematopoietic cells mobilized from bone marrow 12, 15–17 , or from endothelial cells by the process of endothelial to mesenchymal transition (EndoMT) 18, 19 . Recent studies suggest that a subpopulation of heart-infiltrating BM-derived CD45 + cells expressing prominin 1 and other stem cell markers (such as cKit and Sca1), contribute to myoFB differentiation under the influence of pro-fibrotic factors TGFβ 15, 20, 21 .…”

Section: Introductionmentioning

confidence: 99%

Interleukin-10 Inhibits Bone Marrow Fibroblast Progenitor Cell–Mediated Cardiac Fibrosis in Pressure-Overloaded Myocardium

et al. 2017

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Background Activated fibroblasts (myofibroblasts; myoFBs) play critical role in cardiac fibrosis; however, their origin in the diseased heart remains unclear warranting further investigation. Recent studies suggest the contribution of bone marrow fibroblast progenitor cells (BM-FPC) in pressure overload (PO)-induced cardiac fibrosis. We have earlier shown that interleukin-10 (IL10) suppresses PO-induced cardiac fibrosis; however, the role of IL10 in inhibition of BM-FPC-mediated cardiac fibrosis is not known. We hypothesized that IL10 inhibits PO-induced homing of BM-FPCs to the heart and their trans-differentiation to myoFBs and thus attenuates cardiac fibrosis. Methods Pressure overload was induced in wild-type (WT) and IL10 knockout (IL10KO) mice by transverse aortic constriction (TAC). To determine the bone marrow origin, chimeric mice were created using eGFP WT mice marrow to the IL10KO mice. For mechanistic studies, fibroblast progenitor cells were isolated from mouse bone marrow. Results Pressure overload enhanced bone marrow fibroblast progenitor cell (BM-FPC) mobilization and homing in IL10KO mice compared to WT mice. Furthermore, WT bone marrow (from eGFP mice) transplantation in BM-depleted IL10KO mice (IL10KO chimeric mice) reduced TAC-induced BM-FPC mobilization compared to IL10KO mice. GFP co-staining with αSMA or collagen 1α in left ventricular tissue sections of IL10KO chimeric mice suggest that myofibroblasts were derived from bone marrow post-TAC. Finally, WT-BMT in IL10KO mice inhibited TAC-induced cardiac fibrosis and improved heart function. At the molecular level, IL10 treatment significantly inhibited TGFβ-induced transdifferentiation and fibrotic signaling in WT BM-FPC in vitro. Furthermore, fibrosis-associated miRNAs expression was highly upregulated in IL10KO-FPCs compared to WT-FPCs. PCR-based selective miRNA analysis revealed that TGFβ-induced enhanced expression of fibrosis-associated miRNAs (miRNA-21, -145 and -208) was significantly inhibited by IL10. Restoration of miRNA-21 levels suppressed the IL10 effects on TGFβ-induced fibrotic signaling in BM-FPC. Conclusion Our findings suggest that IL10 inhibits BM-FPC homing and trans-differentiation to myofibroblasts in pressure overloaded myocardium. Mechanistically for the first time we showed that IL10 suppresses Smad-miRNA-21 mediated activation of BM-FPCs and thus modulates cardiac fibrosis.

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Section: Introductionmentioning

confidence: 99%

Interleukin-10 Inhibits Bone Marrow Fibroblast Progenitor Cell–Mediated Cardiac Fibrosis in Pressure-Overloaded Myocardium

et al. 2017

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“…It has previously been reported that this protection reaction has been achieved through one‐step processes 7–28. However, these transformations require high temperature,7 extended reaction times,8–15 metal catalysts16–27 or stoichiometric catalysis 28. Recently, the organocatalytic synthesis of 4,6‐benzylidene glycosides from aromatic aldehydes in one step under mild conditions was reported by Schmidt and co‐workers 29.…”

Section: Introductionmentioning

confidence: 99%

Lipase‐Catalyzed Synthesis of Substituted Phenylacetamides: Hammett Analysis and Computational Study of the Enzymatic Aminolysis

2014

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A series of hydroxy‐, methoxy‐, and nitrophenylacetamides was synthesized by enzyme catalysis. The 28 new products were obtained through a lipase‐catalyzed two‐step reaction in very good to excellent yield. In the case of nitro derivatives, a one‐pot, two‐step methodology allowed the desired products to be obtained in high yields. The influence of various reaction parameters in the lipase‐catalyzed reactions, such as enzyme source, nucleophile (alcohol or amine)/substrate ratio, enzyme/substrate ratio, solvent and temperature were studied. It was observed that nitro‐substituted phenylacetates were more reactive in the aminolysis reaction than phenylacetates substituted with a hydroxyl group. To study this substituent effect, a Hammett analysis and the determination of the ρ parameter were carried out. Moreover, a computational study was applied to the most representative systems, performing an exploration of the potential energy surface for the catalyzed and noncatalyzed aminolysis reaction for nitro‐ and hydroxyphenylacetates. Both analysis showed that the presence of a strongly electron‐attracting group favors the activity of the enzyme, in complete agreement with the experimental results of the enzymatic catalysis.

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“…More specifically, developing environment-friendly, convenient, efficient and highly regioselective carbohydrate protection methods remains as one of the most prominent challenges [9]. Over the last several decades, many protection methods have been developed, including the use of reagents such as organotin [10][11][12], organoboron [13,14], organosilicon [15][16][17], metal salts [18][19][20][21][22][23], organobase [24][25][26], and enzymes [27][28][29][30]. Although these reagents each have advantages, they also possess troublesome shortcomings including inherent toxicity, high cost and the necessity to pre-protect secondary hydroxyl groups.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

Hou

Ren

et al. 2016

Molecules

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Abstract:A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly used protecting bulky groups for primary hydroxyl groups, the benzoyl protective group offers a new protection strategy.

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Iron(iii) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides

Abstract: Tandem catalysis by using iron(III) chloride hexahydrate leads to carbohydrate building blocks displaying an orthogonal protecting group pattern as illustrated by the regioselective protection of trehalose and maltose disaccharides.

Cited by 78 publications

References 38 publications

Interleukin-10 Inhibits Bone Marrow Fibroblast Progenitor Cell–Mediated Cardiac Fibrosis in Pressure-Overloaded Myocardium

Interleukin-10 Inhibits Bone Marrow Fibroblast Progenitor Cell–Mediated Cardiac Fibrosis in Pressure-Overloaded Myocardium

Lipase‐Catalyzed Synthesis of Substituted Phenylacetamides: Hammett Analysis and Computational Study of the Enzymatic Aminolysis

Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

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