Stimuli‐Responsive Supramolecular Gelation in Ferrocene–Peptide Conjugates

Afrasiabi, Rouzbeh; Kraatz, Heinz‐Bernhard

doi:10.1002/chem.201302450

Cited by 44 publications

(36 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…More recently, a series of mono‐ and disubstituted ferrocene peptide derivatives have shown self‐assembly and gelation behaviour , . To be able to control the self‐assembly of these structures, it is important to understand the intermolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

“…In contrast, with 1,1′‐disubstituted templates, the conformational preferences of monosubstituted ferrocenes are driven mainly by intermolecular hydrogen bonding . To date, only three monosubstituted ferrocene–peptide conjugates, all derived from ferrocenecarboxylic acid, have shown the ability to form secondary structures similar to those of natural peptides.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Conformational Study of Monosubstituted Aminoferrocene‐Based Peptides Bearing Homo‐ and Heterochiral Pro‐Ala Sequences

et al. 2016

View full text Add to dashboard Cite

Abstract:The synthesis and conformational analysis of a series of the monosubstituted aminoferrocene-based peptides bearing homo-and heterochiral Pro-Ala sequences are described. A change of the Pro amino acid chirality can affect the secondary structure. The homochiral derivatives of tBuCO-AA 2 -AA 1 -NHFc (Fc = ferrocene; AA = Pro, Ala) favour -turns, and a disruption of the secondary structure is observed for the heterochiral analogues in solution. A detailed computational study suggested that γ-turns form in the heterochiral derivatives. The X-ray-de-

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Conformational Study of Monosubstituted Aminoferrocene‐Based Peptides Bearing Homo‐ and Heterochiral Pro‐Ala Sequences

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Introducing a ferrocenyl moiety on to a peptide chain can induce certain secondary structures leading to foldamers , which can function as electrochemical probes, and such peptides are also known to form stimuli‐responsive supramolecular devices like gels . In order to demonstrate the applicability of the synthesized ferrocenyl amino acids, 5b was subjected to base hydrolysis and was coupled with the dipeptide H‐L‐Ala‐L‐Phe‐OMe under standard peptide coupling conditions using HOBt, EDC and DIPEA in DCM to form the tripeptide 6 in 70% yield, with the ferrocenyl residue attached at the N ‐terminus (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Ferrocene‐peptide conjugates that can form functional materials like stimuli‐responsive gels were reported by H. B Kraatz et al . , and A. M. Papini et al . have reported ferrocenyl glycopeptides as electrochemical probes to detect autoantibodies .…”

Section: Introductionmentioning

confidence: 98%

Synthesis of stableC-linked ferrocenyl amino acids and their use in solution-phase peptide synthesis

2015

View full text Add to dashboard Cite

Incorporation of ferrocenyl group to peptides is an efficient method to alter their hydrophobicity. Ferrocenyl group can also act as an electrochemical probe when incorporated onto functional peptides. Most often, ferrocene is incorporated onto peptides post-synthesis via amide, ester or triazole linkages. Stable amino acids containing ferrocene as a C-linked side chain are potentially useful building units for the synthesis of ferrocene-containing peptides. We report here an efficient route to synthesize ferrocene-containing amino acids that are stable and can be used in peptide synthesis. Coupling of 2-ferrocenyl-1,3-dithiane and iodides derived from aspartic acid or glutamic acid using n-butyllithium leads to the incorporation of a ferrocenyl unit to the δ-position or ε-position of an α-amino acid. The reduction or hydrolysis of the dithiane group yields an alkyl or an oxo derivative. The usability of the synthesized amino acids is demonstrated by incorporating one of the amino acids in both C-terminus and N-terminus of tripeptides in solution phase.

show abstract

“…However, the addition of an alkyl spacer, separating the Fc and the peptide allows ultrasound‐triggered gel formation. The two conjugates FcCO‐NH‐(CH 2 ) 6 ‐NH‐Lys( Z )‐Phe‐NHBoc and FcCO‐NH‐(CH 2 ) 6 ‐NH‐Lys( Z )‐Phe‐NHBoc form organogels in toluene with a nanofiber and nanotape morphology, respectively . The addition of a photo‐responsive diazobenzene group to the system provides an additional input that allows structural triggering through light.…”

Section: Metals and Peptide Gelsmentioning

confidence: 99%

Supramolecular Assembly of Peptide and Metallopeptide Gelators and Their Stimuli‐Responsive Properties in Biomedical Applications

Falcone

Kraatz

2018

Chemistry A European J

View full text Add to dashboard Cite

Supramolecular gels are a fascinating class of soft materials that have attracted significant attention in recent years. They are composed of small molecule gelators that assemble into supramolecular network structures. The resulting space is filled with solvent. Some gel materials are able to respond to various stimuli making them attractive drug delivery vehicles and as matrices for tissue regeneration. Peptide-based gel materials are particularly attractive as they possess numerous advantages including biocompatibility and biodegradability. Stimuli-responsive peptides that alter properties as a function of pH, redox, temperature, and enzymes offer the potential to create materials with tunable characteristics. In addition, the ability of metal ions to improve the strength of gelation or act as a scaffold has become an interesting approach to develop dynamic peptide gel materials. In this review, the stimuli-responsive properties (pH, redox, temperature, and enzyme responsive properties), as well as the biocompatible/-degradable nature of the peptide gelators are highlighted. In addition, metal ions are discussed as a stimulus to enhance peptide gelation and a number of potential applications of these peptide gelators are provided with an outlook on future directions.

show abstract

Stimuli‐Responsive Supramolecular Gelation in Ferrocene–Peptide Conjugates

Cited by 44 publications

References 40 publications

Synthesis and Conformational Study of Monosubstituted Aminoferrocene‐Based Peptides Bearing Homo‐ and Heterochiral Pro‐Ala Sequences

Synthesis and Conformational Study of Monosubstituted Aminoferrocene‐Based Peptides Bearing Homo‐ and Heterochiral Pro‐Ala Sequences

Synthesis of stableC-linked ferrocenyl amino acids and their use in solution-phase peptide synthesis

Supramolecular Assembly of Peptide and Metallopeptide Gelators and Their Stimuli‐Responsive Properties in Biomedical Applications

Contact Info

Product

Resources

About