d-Glucosamine in a chimeric prolinamide organocatalyst for direct asymmetric aldol addition

Nisco, Mauro De; Pedatella, Silvana; Bektaş, Semiha; Nucci, Ada; Caputo, Romualdo

doi:10.1016/j.carres.2012.03.041

Cited by 27 publications

(24 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[5] For the macrocyclization of diglycoside 3 its protecting groups were removed by the reaction with activated powdered zinc in glacial acetic acid, and diglycoside 4 were obtained in 87 % yield. † 2 atoms of glucosamine residues were shifted upfield in keeping with the literature data, [6,7] and resonated as a doublet of doublets at 2. Macrocyclic Glycoterpenoid with Glucosamine and Isosteviol Moieties was assayed.…”

supporting

confidence: 83%

The First Macrocyclic Glycoterpenoid Having Glucosamine and Isosteviol Moieties

Garifullin¹,

Strobykina²,

Sharipova³

et al. 2016

MHC

View full text Add to dashboard Cite

show abstract

supporting

confidence: 83%

The First Macrocyclic Glycoterpenoid Having Glucosamine and Isosteviol Moieties

Garifullin¹,

Strobykina²,

Sharipova³

et al. 2016

MHC

View full text Add to dashboard Cite

show abstract

“…Either secondary or primary amino acids have proven to be useful organocatalyst for direct aldol reactions . In recent years, L ‐proline and derivatives have been frequently developed for aldol and many other reactions . Proline is a privileged catalyst able to promote various highly enantioselective transformations .…”

Section: Introductionmentioning

confidence: 99%

Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media

et al. 2013

View full text Add to dashboard Cite

A series of tripeptide organocatalysts containing a secondary amine group and two amino acids with polar side chain units were developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. The effectiveness of short polar peptides as asymmetric catalysts in aldol reactions to attain high yields of enantio- and diastereoselective isomers were investigated. In a comparison, glutamic acid and histidine produced higher % ee and yields when they were applied as the second amino acid in short trimeric peptides. These short polar peptides were found to be efficient organocatalysts for the asymmetric aldol addition reaction in aqueous media.

show abstract

“…GA is a potent inhibitor for several types of tumor cells and acts without influencing normal cells [6,7,8,9]. The difference in reactivity between amino and hydroxyl groups in GA allows regioselectivity to synthesize derivatization with new features and functions [10,11,12]. These synthetic GA derivatives have demonstrated potent biological activity and are used in medicinal research [13,14,15,16,17].…”

Section: Introductionmentioning

confidence: 99%

End-Functionalized Poly(N-isopropylacrylamide) with d-Glucosamine through Different Initiator from C-1 and C-2 Positions via Atom Transfer Radical Polymerization

et al. 2016

View full text Add to dashboard Cite

Regioselective modification of d-glucosamine (2-amino-2-deoxy-d-glucopyranose, GA) through C-1 and C-2 positions to synthesized thermo-responsive D-Glucosamine-poly(N-iso-propylacrylamide) (PNIPAM) via atom transfer radical polymerization (ATRP) was investigated for the first time. Two different schemes of the synthesis for GA derivatives (GA-PNIPAM (i) and (ii)) with well-defined structures using 3,4,6-tri-o-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranose and 1,3,4,6-tetra-o-acetyl-2-amino-2-deoxy-β-d-glucopyranose intermediates were examined. The GA-PNIPAM (ii) had an amino at C-2 position, while there was a hydroxyl in GA-PNIPAM (i) at this position. Both the resulting oligomers (i) and (ii) had a narrow dispersity, and no significant cytotoxic response of copolymers (i) and (ii) was observed in the cell line over the concentration range from 0.1 μg/mL to 1000 μg/mL at any of the exposure times. In addition, it was discovered that GA-PNIPAM (i) and (ii) inhibited the proliferation of Human Hepatocellular Carcinoma Cells HepG2 as the concentration and the time changed, and the inhibitory activity of polymer (ii) was higher than that of he (i). The results suggest that the GA-PNIPAM polymers show excellent biocompatibility in vitro.

show abstract

d-Glucosamine in a chimeric prolinamide organocatalyst for direct asymmetric aldol addition

Cited by 27 publications

References 48 publications

The First Macrocyclic Glycoterpenoid Having Glucosamine and Isosteviol Moieties

The First Macrocyclic Glycoterpenoid Having Glucosamine and Isosteviol Moieties

Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media

End-Functionalized Poly(N-isopropylacrylamide) with d-Glucosamine through Different Initiator from C-1 and C-2 Positions via Atom Transfer Radical Polymerization

Contact Info

Product

Resources

About