Advertisement

Topics

Twisted Macrocycles with Folded ortho-Phenylene Subunits.

08:00 EDT 17th March 2017 | BioPortfolio

Summary of "Twisted Macrocycles with Folded ortho-Phenylene Subunits."

Many foldamers, oligomers that adopt well-defined secondary structures, are now known, including many exhibiting functional behavior. However, examples of foldamer subunits within larger architectures remain rare, despite the importance of higher-order structure in biomacromolecules. Here, we investigate the dynamic covalent assembly of short o-phenylenes, a simple class of aromatic foldamers, into twisted macrocycles. o-Phenylene tetramers have been combined with rod-shaped p-phenylene-, tolane-, and diphenylbutadiyene-based linkers using imine formation. Macrocyclization proceeds efficiently, inducing folding of the o-phenylenes. The resulting [3+3] macrocycles (three o-phenylenes and three linkers) are shape-persistent, triangular structures with twisted cores and internal diameters up to approximately 2 nm. The homochiral D3-symmetric and heterochiral C2-symmetric conformers can be distinguished by NMR spectroscopy. Analysis of the conformational distribution for the p-phenylene-linked macrocycle suggests that the o-phenylene units are largely decoupled, with the less-symmetrical configuration therefore entropically favored. Conformational dynamics were assessed by variable-temperature NMR spectroscopy. Confinement within the macrocyclic architecture slows the inversion of the o-phenylene moieties.

Affiliation

Journal Details

This article was published in the following journal.

Name: Journal of the American Chemical Society
ISSN: 1520-5126
Pages:

Links

DeepDyve research library

PubMed Articles [1015 Associated PubMed Articles listed on BioPortfolio]

Cycloparaphenylenes and Their Catenanes: Complex Macrocycles Unveiled by Ion Mobility Mass Spectrometry.

The insoluble product mixture obtained from cycloparaphenylene (CPP) synthesis from Suzuki coupling and reductive aromatization was analyzed. Traditional mass spectrometry suggests a homologous series...

Hexagonal Molecular Tiling by Hexagonal Macrocycles at the Liquid/Solid Interface: Structural Effects on Packing Geometry.

We present here hexagonal tiling using hexagonal phenylene-ethynylene and phenylene-butadiynylene macrocycles attached by alkyl ester groups, PEM-C6 and PBM-C8, respectively, or triethylene glycol est...

Synthesis and Bowl-in-Bowl Assembly of a Geodesic Phenylene Bowl.

A phenylene multiring with a corannulenoidal skeleton was synthesized. Geodesic constraints over 20 phenylene panels resulted in its nanometer-sized, bowl-shaped molecular structure, which was unequiv...

Trichalcogenasumanene ortho-Quinones: Synthesis, Properties, and Transformation for Various Hetero Polycycles.

The region-selective transformation of heterabuckybowl trichalcogenasumanenes (1a/1b) was conducted on the peripheral butoxy groups to afford trichalcogenasumanene ortho-quinones (2a/2b). Compounds 2a...

Coordination-Driven Self-Assembly of Ionic Irregular Hexagonal Metallamacrocycles via an Organometallic Clip and Their Cytotoxicity Potency.

Two new irregular hexagons (6 and 7) were synthesized from a pyrazine motif containing an organometallic acceptor clip [bearing platinum(II) centers] and different neutral donor ligands (4,4'-bipyridi...

Clinical Trials [63 Associated Clinical Trials listed on BioPortfolio]

To Compare SH T00658ID Over Ortho Tri-Cyclen Lo (US/Canada)

The objective of the study is to compare the oral contraceptive (OC) SH T00658ID over Ortho Tri-Cyclen Lo administered for 13 cycles to healthy female volunteers between 18 and 50 years of...

Combined Atropine With Orthokeratology in Childhood Myopia Control (AOK) -A Randomized Controlled Trial

This study aims to compare effects in retardation of myopia progression of combined ortho-k and 0.01% atropine therapy with those of ortho-k alone.Myopia control methods mainly focus on op...

Investigation of the Effect of Short-term Orthokeratology With Increased Compression Factor on Ocular Parameters

Orthokeratology (ortho-k) is a clinical technique that uses reverse geometry rigid gas permeable contact lens exerting positive pressure on the central cornea to temporary reduce refractiv...

Study to Assess the Effect of BMS-790052 on the Pharmacokinetics of Ortho Tri-Cyclen® in Healthy Female Subjects

The purpose of this study is to assess the effect of BMS-790052 on the pharmacokinetics of Ortho Tri-Cyclen® in healthy female subjects.

Atazanavir and Ritonavir (ATV/RTV) and an Oral Contraceptive in Healthy Females

The purpose of this study is to administer a combined oral contraceptive (ethinyl estradiol and norgestimate) with the HIV treatment of atazanavir and ritonavir to healthy females in order...

Medical and Biotech [MESH] Definitions

Protein translocase in BACTERIA or CHLOROPLASTS that exports or secretes folded proteins. In GRAM-NEGATIVE BACTERIA, twin-arginine translocase (TAT) is involved in the export of folded proteins to the PERIPLASM. In chloroplasts, TAT is involved in transporting folded proteins across the membranes of THYLAKOIDS.

One ring heterocyclic compounds defined by C6H7NO. Permitted are any degree of hydrogenation, any substituents and any ortho-fused or ortho-peri-fused ring systems.

Gram-negative bacterial secretion systems which carry out the secretion of folded proteins.T2SSs secrete folded proteins from the PERIPLASMIC SPACE that have been exported there by SEC TRANSLOCASE or TAT SECRETION SYSTEMS, or they secrete folded proteins directly from the CYTOPLASM. The T2SSs have four substructures, an ATPase, an inner membrane platform, a pseudopilin, and secretin, an outer membrane complex which is a channel for secretion. (This bacterial secretin is not the same as the mammalian hormone also named SECRETIN.)

A general class of ortho-dihydroxyphenylalkylamines derived from tyrosine.

Single chains of amino acids that are the units of multimeric PROTEINS. Multimeric proteins can be composed of identical or non-identical subunits. One or more monomeric subunits may compose a protomer which itself is a subunit structure of a larger assembly.

Quick Search
Advertisement
 


DeepDyve research library

Searches Linking to this Article