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 [974 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...

m-Phenylene-Linked Dipyrrins and Their Boron-Difluoride Complexes as Variously Shaped Macrocyclic Oligomers.

The effectiveness of a m-phenylene linker, which has rigidity as well as rotational flexibility, is presented to produce a series of variously shaped macrocyclic oligomers of dipyrrins and BODIPYs, wh...

Solvent effects on the folding of o-phenylene oligomers.

ortho-Phenylene oligomers fold into compact helical conformations in solution, and have therefore recently emerged as a class of foldamers. Previous work has shown that their folding is controlled by ...

Fused helicene chains: towards twisted graphene nanoribbons.

Taking advantage of an unexpected regioselectivity of intramolecular Scholl reactions on penta-phenylene compounds that favors distorted [5]helicenes over their flat couterparts, a new synthetic appro...

Solvent-Templated Folding of Perylene Bisimide Macrocycles into Coiled Double-String Ropes with Solvent-Sensitive Optical Signatures.

A series of semi-rigid perylene bisimide (PBI) macrocycles with varied ring size containing two to nine PBI chromophores were synthesized in a one-pot reaction and their photophysical properties were ...

Clinical Trials [59 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