Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (S-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and 1H NMR spectroscopy. This work demonstrates the first case of using S-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of S-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.

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Importance of Hydrolysis of Amino Acid Moiety in Water-Soluble Prodrugs of Disodium Cromoglycate for Increased Oral Bioavailability.

Journal of Pharmacobio-Dynamics ◽

10.1248/bpb1978.15.339 ◽

1992 ◽

Vol 15 (7) ◽

pp. 339-345 ◽

Cited By ~ 8

Author(s):

Akihisa YOSHIMI ◽

Hiroyuki HASHIZUME ◽

Satoshi TAMAKI ◽

Hirokazu TSUDA ◽

Fumio FUKATA ◽

...

Keyword(s):

Amino Acid ◽

Oral Bioavailability ◽

Water Soluble ◽

Disodium Cromoglycate ◽

Acid Moiety ◽

Amino Acid Moiety ◽

Hydrolysis Of

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Synthesis and antimicrobial activity of some novel 1,2-dihydro-[1,2,4]triazolo[1,5-a]pyrimidines bearing amino acid moiety

RSC Advances ◽

10.1039/d0ra08189b ◽

2021 ◽

Vol 11 (5) ◽

pp. 2905-2916

Author(s):

Mounir A. A. Mohamed ◽

Adnan A. Bekhit ◽

Omyma A. Abd Allah ◽

Asmaa M. Kadry ◽

Tamer M. Ibrahim ◽

...

Keyword(s):

Antimicrobial Activity ◽

Amino Acid ◽

Green Chemistry ◽

Antimicrobial Activities ◽

Amino Acid Derivatives ◽

Acid Moiety ◽

Amino Acid Moiety

A new series of [1,2,4]-triazole bearing amino acid derivatives were synthesized under green chemistry conditions and evaluated for their antimicrobial activities.

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Engineering two mutants of cDNA-encoding G2 subunit of soybean glycinin capable of self-assembly in vitro and rich in methionine

Biologia ◽

10.2478/s11756-007-0097-1 ◽

2007 ◽

Vol 62 (4) ◽

Author(s):

Reda Sammour

Keyword(s):

Amino Acid ◽

Self Assembly ◽

Seed Quality ◽

Amino Acid Residues ◽

Methionine Residues

AbstractThe main goal of this work was to make the cDNA-encoding subunit G2 of soybean glycinin, capable of self-assembly in vitro and rich in methionine residues. Two mutants (pSP65/G4SacG2 and pSP65/G4SacG2HG4) were therefore constructed. The constructed mutants were successfully assembled in vitro into oligomers similar to those occurred in the seed. The successful self-assembly was due to the introduction of Sac fragment of Gy4 (the codons of the first 21 amino acid residues), which reported to be the key element in self-assembly into trimers. The mutant pSP65/G4SacG2HG4 included the acidic chain of Gy4 (HG4), which was previously molecularly modified to have three methionine residues. This mutant will be useful in the efforts to improve the seed quality.

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4-alkoxycarbonyloxazoles as β-hydroxy-α-amino acid synthons: efficient stereoselective syntheses of 3-amino-2,3,6-trideoxyhexoses and a hydroxy amino acid moiety of Al-77-B

Tetrahedron ◽

10.1016/s0040-4020(01)85597-6 ◽

1990 ◽

Vol 46 (13-14) ◽

pp. 4823-4846 ◽

Cited By ~ 45

Author(s):

Yasumasa Hamada ◽

Akiyoshi Kawai ◽

Toshiaki Matsui ◽

Osamu Hara ◽

Takayuki Shioiri

Keyword(s):

Amino Acid ◽

Acid Moiety ◽

Hydroxy Amino Acid ◽

Hydroxy Amino ◽

Amino Acid Moiety ◽

Stereoselective Syntheses

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(±)-CSA catalyzed Friedel–Crafts alkylation of indoles with 3-ethoxycarbonyl-3-hydoxyisoindolin-1-one: an easy access of 3-ethoxycarbonyl-3-indolylisoindolin-1-ones bearing a quaternary α-amino acid moiety

Tetrahedron Letters ◽

10.1016/j.tetlet.2013.01.010 ◽

2013 ◽

Vol 54 (11) ◽

pp. 1444-1448 ◽

Cited By ~ 21

Author(s):

Anvita Srivastava ◽

Shivendra Singh ◽

Sampak Samanta

Keyword(s):

Amino Acid ◽

Easy Access ◽

Acid Moiety ◽

Amino Acid Moiety

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Lossen Rearrangement by Rh(III)-Catalyzed C-H Activation/Annulation of Aryl Hydroxamates with Alkynes: Access to Quinolone-containing Amino Acid Derivatives

Organic & Biomolecular Chemistry ◽

10.1039/d1ob01711j ◽

2021 ◽

Author(s):

Dmitry A. Petropavlovskikh ◽

Daria Vorobyeva ◽

Ivan A. Godovikov ◽

Sergey E Nefedov ◽

Oleg A. Filippov ◽

...

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Robust Method ◽

Acid Moiety ◽

Internal Alkynes ◽

Amino Acid Moiety

A convenient and robust method for the preparation of new CF3-containing 2-quinolones has been developed via Rh(III)-catalyzed C-H activation/Lossen rearrangement/annulation cascade of N-pivaloyloxy-arylamides with internal alkynes bearing α-CF3-α-amino acid moiety...

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Acrylamide Formation in Food: A Mechanistic Perspective

Journal of AOAC International ◽

10.1093/jaoac/88.1.262 ◽

2005 ◽

Vol 88 (1) ◽

pp. 262-267 ◽

Cited By ~ 82

Author(s):

Varoujan A Yaylayan ◽

Richard H Stadler

Keyword(s):

Amino Acid ◽

Carbonyl Compounds ◽

Azomethine Ylide ◽

Significant Progress ◽

Acid Moiety ◽

Sugar Moiety ◽

Acrylamide Formation ◽

Amino Acid Moiety ◽

Strecker Aldehyde

Abstract Earliest reports on the origin of acrylamide in food have confirmed asparagine as the main amino acid responsible for its formation. Available evidence suggests that sugars and other carbonyl compounds play a specific role in the decarboxylation process of asparagine, a necessary step in the generation of acrylamide. It has been proposed that Schiff base intermediate formed between asparagine and the sugar provides a low energy alternative to the decarboxylation from the intact Amadori product through generation and decomposition of oxazolidin-5-one intermediate, leading to the formation of a relatively stable azomethine ylide. Literature data indicate the propensity of such protonated ylides to undergo irreversible 1,2-prototropic shift and produce, in this case, decarboxylated Schiff bases which can easily rearrange into E Decarboxylated Amadori products can either undergo the well known β-elimination process initiated by the sugar moiety to produce 3-aminopropanamide and 1-deoxyglucosone or undergo 1,2-elimination initiated by the amino acid moiety to directly generate acrylamide. On the other hand, the Schiff intermediate can either hydrolyze and release 3-aminopropanamide or similarly undergo amino acid initiated 1,2-elimination to directly form acrylamide. Other thermolytic pathways to acrylamide—considered marginal at this stage—via the Strecker aldehyde, acrolein, and acrylic acid, are also addressed. Despite significant progress in the understanding of the mechanistic aspects of acrylamide formation, concrete evidence for the role of the different proposed intermediates in foods is still lacking.

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Insight into the self-assembly of water-soluble perylene bisimide derivatives through a combined computational and experimental approach

Nanoscale ◽

10.1039/c9nr03898a ◽

2019 ◽

Vol 11 (34) ◽

pp. 15917-15928 ◽

Cited By ~ 5

Author(s):

Emily R. Draper ◽

Liam Wilbraham ◽

Dave J. Adams ◽

Matthew Wallace ◽

Ralf Schweins ◽

...

Keyword(s):

Amino Acid ◽

Self Assembly ◽

Experimental Approach ◽

Water Soluble ◽

The Self ◽

Experimental Techniques ◽

Perylene Bisimide ◽

Perylene Bisimides ◽

Insight Into

We use a combination of computational and experimental techniques to study the self-assembly and gelation of amino-acid functionalised water-soluble perylene bisimides.

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