scholarly journals Metal-Binding Q-Proline Macrocycles

2021 ◽  
Author(s):  
Justin Northrup ◽  
Jesse Wiener ◽  
Matthew Hurley ◽  
Chun-Feng David Hou ◽  
Taylor Keller ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Functional Groups ◽  
Metal Cation ◽  
Metal Binding ◽  
Metal Cations ◽  
Efficient Synthesis ◽  
Steric Interactions ◽  
Fmoc Spps

Herein, we introduce the efficient synthesis of Q-proline (Q-Pro) based, metal-binding macrocycles (QPM), which can display up to nine functional groups. Synthesis of eight QPM was achieved through standard Fmoc-SPPS and peptoid chemistry. QPM are disordered in the absence of a metal cation, as evidenced by NMR and a crystal structure of <b>QPM-3</b> obtained through racemic crystallization. Addition of metal cations cause these macrocycles to adopt ordered, uniform core structures regardless of the functional groups. Alkylation of QPM allows for addition of reactive functional groups as the final step in a synthesis. Interestingly, the addition of secondary functional groups to the hydantoin amide position (R<sub>2</sub>) converts the proline ring from Cg-endo to Cg-exo, due to steric interactions.

scholarly journals Metal-Binding Q-Proline Macrocycles

2021 ◽  
Author(s):  
Justin Northrup ◽  
Jesse Wiener ◽  
Matthew Hurley ◽  
Chun-Feng David Hou ◽  
Taylor Keller ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Functional Groups ◽  
Metal Cation ◽  
Metal Binding ◽  
Metal Cations ◽  
Efficient Synthesis ◽  
Steric Interactions ◽  
Fmoc Spps

Herein, we introduce the efficient synthesis of Q-proline (Q-Pro) based, metal-binding macrocycles (QPM), which can display up to nine functional groups. Synthesis of eight QPM was achieved through standard Fmoc-SPPS and peptoid chemistry. QPM are disordered in the absence of a metal cation, as evidenced by NMR and a crystal structure of <b>QPM-3</b> obtained through racemic crystallization. Addition of metal cations cause these macrocycles to adopt ordered, uniform core structures regardless of the functional groups. Alkylation of QPM allows for addition of reactive functional groups as the final step in a synthesis. Interestingly, the addition of secondary functional groups to the hydantoin amide position (R<sub>2</sub>) converts the proline ring from Cg-endo to Cg-exo, due to steric interactions.

scholarly journals Synthesis and metal binding properties of N-alkylcarboxyspiropyrans

2017 ◽  
Vol 13 ◽  
pp. 1542-1550 ◽  
Author(s):  
Alexis Perry ◽  
Christina J Kousseff
Keyword(s):  
Metal Binding ◽  
Metal Cations ◽  
Efficient Synthesis ◽  
Visible Spectroscopy ◽  
Binding Properties ◽  
Systematic Analysis ◽  
H Nmr ◽  
Common Structure ◽  
Photoactive Materials ◽  
Uv Visible

Spiropyrans bearing an N-alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2–12 carbon atom alkylcarboxylate substituents, and a systematic analysis of their interactions with metal cations using 1H NMR and UV-visible spectroscopy. All N-alkylcarboxyspiropyrans in this study displayed a strong preference for binding divalent metal cations and a modest increase in M2+ binding affinity correlated with increased alkycarboxylate tether length.

scholarly journals Crystal Structure of Exotoxin A from Aeromonas Pathogenic Species

Toxins ◽  
2020 ◽  
Vol 12 (6) ◽  
pp. 397 ◽  
Author(s):  
Geoffrey Masuyer
Keyword(s):  
Crystal Structure ◽  
Metal Binding ◽  
Elongation Factor ◽  
Pathogenic Species ◽  
Exotoxin A ◽  
Pseudomonas Exotoxin A ◽  
Eukaryotic Elongation Factor 2 ◽  
Eukaryotic Elongation Factor ◽  
Bacterial Virulence Factor ◽  
Interdomain Interactions

Aeromonas exotoxin A (AE) is a bacterial virulence factor recently discovered in a clinical case of necrotising fasciitis caused by the flesh-eating Aeromonas hydrophila. Here, database mining shows that AE is present in the genome of several emerging Aeromonas pathogenic species. The X-ray crystal structure of AE was solved at 2.3 Å and presents all the hallmarks common to diphthamide-specific mono-ADP-ribosylating toxins, suggesting AE is a fourth member of this family alongside the diphtheria toxin, Pseudomonas exotoxin A and cholix. Structural homology indicates AE may use a similar mechanism of cytotoxicity that targets eukaryotic elongation factor 2 and thus inhibition of protein synthesis. The structure of AE also highlights unique features including a metal binding site, and a negatively charged cleft that could play a role in interdomain interactions and may affect toxicity. This study raises new opportunities to engineer alternative toxin-based molecules with pharmaceutical potential.

Wechselwirkungen in Molekülkristallen, 160 [1,2]. Kristallzüchtung und Strukturbestimmung der verschiedenartigen Polyphenyl-Kontaktionenmultipel [p-Quaterphenylee⊖⊖][Na⊕(DME)3]2, [p-Quaterphenyl⊖⊖(Na⊕(THF)3)2] und [p-Terphenyl⊖⊖Na⊕(DME)2Na⊕(DME)]2 / Interaction in Molecular Crystals, 160 [1, 2]. Crystallization and Structure Determination of the Different Polyphenyl Contact Ion Multiples [p-Quaterphenylee⊖⊖][Na⊕(DME)3]2, [p-Quaterphenyl⊖⊖(Na⊕(THF)3)2] und [p-Terphenyl⊖⊖Na⊕(DME)2Na⊕(DME)]2

2000 ◽  
Vol 55 (12) ◽  
pp. 1103-1113 ◽  
Author(s):  
Hans Bock ◽  
K. Gharagozloo-Hubmann ◽  
M. Sievert
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Sodium Salt ◽  
Structure Determination ◽  
Metal Cation ◽  
Molecular Crystals ◽  
Sodium Salts ◽  
Structure Determinations ◽  
Cation Coordination

The π-hydrocarbons p-terphenyl and p-quaterphenyl are reduced to their dianions in aprotic solutions of different ethers at sodium metal mirrors. Single crystal structure determinations of the solvent-separated or solvens-shared contact ion multiples, [p-terphenyl⊖⊖ Na⊕(DME)2Na⊕DME]2, p-quaterphenyl⊖⊖ ][Na⊕(DME)3]2 and [p-quaterpheny⊖⊖( Na⊕(THF)3)2], prove the essential cation solvation by the chelating dimethoxyethane (DME) versus the bulky tetrahydrofuran (THF) ligands: The solution network of equilibria between solvent separated and solvent shared ion aggregates can be considerably and transparently modified by the ether solvent selected. In addition, the structures of the monomeric sodium salts reveal partly novel details of metal cation coordination by contacts Na⊕ ··· O as well as Na⊕ ··· Cπ such as in the dimeric sodium salt of p-terphenyl dianion, [(DME)2Na⊕ (terphenyl⊖⊖)(Na⊕ DME)(terphenyl⊖⊖)Na⊕ (DME)2].

scholarly journals N′-Cyclododecylidenepyridine-4-carbohydrazide

2012 ◽  
Vol 68 (4) ◽  
pp. o1205-o1205
Author(s):  
Andreas Lemmerer ◽  
Joel Bernstein ◽  
Volker Kahlenberg
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Functional Groups ◽  
Title Compound ◽  
Antituberculosis Drug ◽  
Compound C

The title compound, C18H27N3O, is a derivative of the antituberculosis drug isoniazid (systematic name: pyridine-4-carbohydrazidei). The crystal structure consists of repeatingC(4) chains along thebaxis, formed by N—H...O hydrogen bonds with adjacent amide functional groups that are related by ab-glide plane. The cyclododecyl ring has the same approximately `square' conformation, as seen in the parent hydrocarbon cyclododecane.

scholarly journals Metal ion influences distortion of the ligand in the structure of [M{2-MeO(O)CC6H4NHC(S)NP(S)(OiPr)2}2] (M = ZnII, CdII) complexes: a driving force for intermolecular aggregation

2015 ◽  
Vol 44 (31) ◽  
pp. 14101-14109 ◽  
Author(s):  
Damir A. Safin ◽  
Maria G. Babashkina ◽  
Michael Bolte ◽  
Mariusz P. Mitoraj ◽  
Axel Klein
Keyword(s):  
Crystal Structure ◽  
Metal Cation ◽  
Driving Force ◽  
Metal Ion ◽  
Supramolecular Aggregation

Reaction of the deprotonated 2-MeO(O)CC6H4NHC(S)NHP(S)(OiPr)2 (HL) with ZnII or CdII leads to [ZnL2] and [CdL2]. The nature of the metal cation (ZnIIvs. CdII) drives the supramolecular aggregation of molecules in the crystal structure.

Eine effiziente Synthesemethode für DiarylallenyIiden(pentacarbonyl)chrom- und -wolfram-Komplexe -Kristallstruktur von (CO)5Cr=C=C=CPh2 / An efficient Synthesis of Diarylallenylidene Pentacarbonyl Chromium and Tungsten Complexes - Crystal Structure of (CO)5Cr=C=C=CPh2

1994 ◽  
Vol 49 (9) ◽  
pp. 1207-1214 ◽  
Author(s):  
Helmut Fischer ◽  
David Reindl ◽  
Gerhard Roth
Keyword(s):  
Crystal Structure ◽  
Structure Analysis ◽  
Good Yield ◽  
Efficient Synthesis ◽  
X Ray ◽  
Tungsten Complexes ◽  
And Tungsten

An efficient synthesis of diarylallenylidene pentacarbonyl chromium and tungsten com­plexes is presented. Irradiation of M(CO)6 in THF affords (CO)sM[THF], Substitution of the THF ligand by diarylpropargylalcoholate and subsequent desoxygenation with COCF gives the title compounds in good yield. (The structure of diphenylallenylidene pentacarbonyl chromium has been determined by X-ray structure analysis

Sign in / Sign up

Export Citation Format

Share Document