Supramolecular Gel Electrophoresis of Acidic Native Proteins

Munenobu, Kanako; Hase, Takayuki; Oyoshi, Takanori; Yamanaka, Masamichi

doi:10.1021/ac5026539

Cited by 22 publications

(20 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, as a result of their facile preparation and diverse self‐assembly morphologies, a number of LMWGs have been reported. For example, Sureshan et al prepared gels by using mannitol derivatives that could selectively and easily remove oil from a mixture of oil and seawater,44 Yamanaka and co‐workers reported that a hydrogel prepared from a tris‐urea derivative with glucose moieties can function as a matrix for the electrophoresis of acidic native proteins45 and Maruyama and co‐workers reported that a gelator precursor, capable of forming a hydrogel after activation by a cancer‐related enzyme, induced selective cytotoxicity towards cancer cells 46…”

Section: Resultsmentioning

confidence: 99%

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

2014

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

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

2014

View full text Add to dashboard Cite

show abstract

“…Recently, as a result of their facile preparation and diverse self-assembly morphologies, a number of LMWGs have been reported. For example, Sureshan et al prepared gels by using mannitol derivatives that could selectively and easily remove oil from a mixture of oil and seawater, [44] Yamanaka and co-workers reported that a hydrogel prepared from a tris-urea derivative with glucose moieties can function as a matrix for the electrophoresis of acidic native proteins [45] and Maruyama and co-workers reported that a gelator precursor, capable of forming a hydrogel after activation by a cancer-related enzyme, induced selective cytotoxicity towards cancer cells. [46] LMWGs of 4,6-benzylidene monosaccharides were first reported by Shinkai and co-workers in 1998, [47] and since then a number of 4,6-benzylidene-glycoside-type gelators have been studied.…”

Section: Gelation Abilities Of the Glucose Derivativesmentioning

confidence: 99%

Mild One‐Step Synthesis of 4,6‐Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives

et al. 2015

View full text Add to dashboard Cite

We report herein an efficient one‐step synthesis of 4,6‐benzylidene glycoside derivatives from aromatic aldehydes bearing electron‐donating or ‐withdrawing groups as well as polymerisable monomer groups. Glucose, mannose and galactose derivatives could also be used successfully. Several of the glucose derivatives thus obtained acted as gelators for various solvents, including water. 4‐(n‐Butoxybenzylidene)glucose derivative 3a produced both a clear squalane gel and a hydrogel at 0.1 wt.‐%. Furthermore, 3‐(n‐butoxybenzylidene)glucose derivative 3i produced a clear organogel and an opaque hydrogel. The critical gelation concentration (CGC) of 3i in squalane was determined to be 0.02 wt.‐%, which is one of the lowest CGC values reported so far. The organogels, hydrogels and aqueous solution gels produced from 3a and 3d exhibited thixotropy. The strength and thixotropy of the organo‐ and hydrogel produced from 3a were estimated by a rheometer. The gel morphologies were observed by field‐emission and wet‐scanning electron microscopy, and the self‐assembly modes were analysed by XRD. We have concluded that super‐gelators can be created by this method.

show abstract

“…[7] Among the building blocks for generating supramolecular hydrogels, peptides [1c,8] are the most explored ones. The current strategies for designing peptidic hydrogelators are to introduce a long alkyl chain, [8a,9] aromatic groups, [8c,10] or residue of opposite charges.…”

mentioning

confidence: 99%

Mixing Biomimetic Heterodimers of Nucleopeptides to Generate Biocompatible and Biostable Supramolecular Hydrogels

Yuan¹,

Du²,

Shi³

et al. 2015

Angew Chem Int Ed

View full text Add to dashboard Cite

As a new class of biomaterials, most of the supramolecular hydrogels formed by small peptides require the attachment of a long alkyl chain, multiple aromatic groups, or strong electrostatic interactions. Based on the fact that the most abundant protein assemblies in nature are dimeric, we select short peptide sequences from the interface of a heterodimer of proteins with known crystal structure to conjugate with nucleobases to form nucleopeptides. Being driven mainly by hydrogen bonds, the nucleopeptides self-assemble to form nanofibers, which results in supramolecular hydrogels upon simple mixing of two distinct nucleopeptides in water. Moreover, besides being biocompatible to mammalian cells, the heterodimer of the nucleopeptides exhibit excellent proteolytic resistance against proteinase K. This work, as the first report that supramolecular hydrogelation triggered by mixing heterodimeric small nucleopeptides, illustrates a new and rational approach to create soft biomaterials.

show abstract

Supramolecular Gel Electrophoresis of Acidic Native Proteins

Cited by 22 publications

References 39 publications

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

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

Mild One‐Step Synthesis of 4,6‐Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives

Mixing Biomimetic Heterodimers of Nucleopeptides to Generate Biocompatible and Biostable Supramolecular Hydrogels

Contact Info

Product

Resources

About