A molecular receptor for zwitterionic phenylalanine.

Org Biomol Chem

Organic Chemistry Department, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain.

Published: April 2016

AI Article Synopsis

  • A new chiral receptor has been developed using a 1,3-ketoenol system combined with two pyridine molecules linked as sulfonamide and carboxamide to a benzofuran structure.
  • This receptor is specifically designed for associating with zwitterionic phenylalanine, a form of the amino acid that carries both positive and negative charges.
  • Unlike traditional methods for extracting amino acids from water, this novel receptor does not require crown ethers, ureas, or guanidiniums, marking a significant advancement in the field.

Article Abstract

The combination of a 1,3-ketoenol system and two pyridine molecules attached as sulfonamide and carboxamide to a benzofuran skeleton allows the preparation of a novel chiral receptor for zwitterionic phenylalanine association. Interestingly, no crown-ether, urea or guanidinium are necessary to carry out the extraction of amino acids from the aqueous solution, which constitutes a breakthrough in comparison with other receptors for zwitterionic amino acid extraction.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c6ob00490cDOI Listing

Publication Analysis

Top Keywords

receptor zwitterionic
8
zwitterionic phenylalanine
8
molecular receptor
4
phenylalanine combination
4
combination 13-ketoenol
4
13-ketoenol system
4
system pyridine
4
pyridine molecules
4
molecules attached
4
attached sulfonamide
4

Similar Publications

Peptide-Guided Assembly of Silver Nanoparticles for the Diagnosis of HER2-Positive Breast Cancer.

Anal Chem

December 2024

State Key Laboratory of Analytical Chemistry for Life Science, School of Life Sciences, Nanjing University, Nanjing 210023, PR China.

Peptide-engineered nanoparticles have great potential for biomedical research and application. In this work, we have designed and fabricated an electrochemical biosensor based on peptide-guided assembly of silver nanoparticles (AgNPs), in which a peptide is endowed with dual functions to recognize target and guide assembly of AgNPs. As a proof of concept, the performance of this biosensor is validated by quantifying human epidermal growth factor receptor 2 (HER2) protein.

View Article and Find Full Text PDF

Site-Selective Zwitterionic Poly(caprolactone-carboxybetaine)-Growth Hormone Receptor Antagonist Conjugate: Synthesis and Biological Evaluation.

Biomacromolecules

December 2024

Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.

Zwitterionic polymers have been found to be biocompatible alternatives to poly(ethylene glycol) (PEG) for conjugation to proteins. This work reports the site-selective conjugation of poly(caprolactone-carboxybetaine) (pCLZ) to human growth hormone receptor antagonist (GHA) B2036-alkyne and investigation of safety, activity, and pharmacokinetics. Azide-end-functionalized pCLZs were synthesized and conjugated to GHA B2036-alkyne via copper-catalyzed click reaction.

View Article and Find Full Text PDF

Insulin Stabilization Designs for Enhanced Therapeutic Efficacy and Accessibility.

Acc Chem Res

November 2024

Division of Endocrinology and Diabetes, Department of Pediatrics, School of Medicine, Stanford University, Stanford, California 94305, United States.

Article Synopsis
  • Insulin has been essential for diabetes treatment since 1921, but its stability is compromised by temperature, transport, and storage challenges, requiring strict cold-chain management that limits access in low-income areas.
  • Despite advancements in insulin formulations, current treatments still present difficulties for patients, necessitating safer and more user-friendly therapies to improve outcomes.
  • Recent research has led to the creation of novel stable insulin analogs and miniaturized formulations that maintain bioactivity while enhancing stability and absorption rates, addressing both stability and usability issues in insulin therapies.*
View Article and Find Full Text PDF

The importance of anions in various processes has led to a search for molecules that can effectively recognize and interact with these anions. This study explores how the tetraglycine [(Gly)] peptide in its zwitterionic, neutral, and terminally capped forms acts as a receptor for HPO and HSO anions within the framework of supramolecular host-guest chemistry. Using molecular dynamics (MD) simulations, we obtained the conformations of the receptor-anion complexes.

View Article and Find Full Text PDF

The research investigates the cytotoxic effects of the stable NH-form of a resorcinol-based Schiff base (HL) and its metal complexes (Zn(II), Cd(II), Cu(II), Ni(II)) on MCF-7 breast cancer cells. The structural characterization was conducted utilizing diverse analytical techniques, including mass spectrometry, elemental analysis, molar conductance, magnetic moment, UV-Vis, IR and ESR. The crystalline state analysis of HL through X-ray crystallography disclosed a hybrid structure comprising two canonical forms, specifically the quinoid and zwitterion, that contribute to resonance and diverse interactions, resulting in the development of a three-dimensional form.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!