Development of Low Molecular Weight Ferrocene–Biotin Bioconjugates as Electrochemical Sensors

Scarborough, J. Hunter; Brusoski, Kara; Brewer, Samantha M.; Rodich, Sean; Chatley, Kevin S.; Nguyen, Trang; Green, Kayla N.

doi:10.1021/om501294f

Cited by 5 publications

(2 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Clearly, such incorporation of an OM unit in the peptide backbone has a significant impact on the physicochemical properties of the peptide. A more advanced building block allowed incorporation into peptides without affecting the native orientation of the backbone: 1′-aminoferrocene-1-carboxylic acid − ( 64 ) was incorporated into small peptides ( 65 , 66 ). − In an elaborate attempt to study the presence of Fc units in the peptidic backbone, even “peptides” were prepared that contain only Fc units; by use of Fmoc-Fc-C(O)OH ( 67 ) and SPPS methods that are common for Fmoc-based SPPS, tri-, tetra-, and penta-“peptides” ( 68 ) were obtained in 12–18% isolated yield (Scheme ). The prepared oligo-Fc “peptides” displayed a stepwise oxidation process, suggesting electronic and electrostatic interactions in these oligomers.…”

Section: Peptide Backbone Modificationsmentioning

confidence: 99%

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

2016

View full text Add to dashboard Cite

Peptides are important biological molecular entities in biomedical research. They can be prepared in a large variety of shapes, with a host of chemical functions, and tailored for specific applications. Organometallic medicinal chemistry is a relatively young field that explores biomedical and bioanalytical applications of organometallic complexes, that is, metal compounds with at least one direct, covalent metal-carbon bond. The conjugation of peptides to such medicinally active organometallic moieties started only about 20 years ago, and it has been very beneficial for the development of bioorganometallic chemistry in general. Similarly, the biomedical properties of peptides have been altered by their conjugation to organometallic (OM) moieties. In this review, synthetic methods by which OM moieties can be conjugated to peptides via a carbon-metal bond are described, and selected medicinal applications of such conjugates are discussed. Inorganic coordination complexes between metal ions and peptides are excluded from this review. Also, the labeling of peptides with radiometals and applications of radiolabeled peptides will not be treated herein. First, modifications of the peptide backbone (either N- or C-terminally, or both) with organometallic moieties will be described, including the insertion of OM moieties as part of the peptide backbone. Then side-chain modifications will be reported, among them the most recent strategies for chemoselective arene metalation on peptides. Finally, approaches by which multiple metalation can be achieved are explored. In each section, selected examples of biological applications are highlighted.

show abstract

Section: Peptide Backbone Modificationsmentioning

confidence: 99%

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

2016

View full text Add to dashboard Cite

show abstract

“…Increasing the length of the carbon chain also reduces the steric hindrance of the biotin rings and facilitates access of the reactive linker, enabling further reactions used in the analysis or in the synthesis. The currently commercially available Ahx derivative in combination with biotin is Fmoc-Lys(biotinyl-ε-aminocaproyl)-OH, used in solid phase peptide synthesis [72][73][74][75][76][77].…”

Section: Ahx As An Element Of Biotinylation Reagentsmentioning

confidence: 99%

The Importance of 6-Aminohexanoic Acid as a Hydrophobic, Flexible Structural Element

Markowska

Markowski²,

Jarocka-Karpowicz

2021

IJMS

View full text Add to dashboard Cite

6-aminohexanoic acid is an ω-amino acid with a hydrophobic, flexible structure. Although the ω-amino acid in question is mainly used clinically as an antifibrinolytic drug, other applications are also interesting and important. This synthetic lysine derivative, without an α-amino group, plays a significant role in chemical synthesis of modified peptides and in the polyamide synthetic fibers (nylon) industry. It is also often used as a linker in various biologically active structures. This review concentrates on the role of 6-aminohexanoic acid in the structure of various molecules.

show abstract

Ferrocenyl chalcogeno (sugar) triazole conjugates: Synthesis, characterization and anticancer properties

Panaka

Trivedi

Jaipal

et al. 2016

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

Development of Low Molecular Weight Ferrocene–Biotin Bioconjugates as Electrochemical Sensors

Abstract: Contents of Supplemental Information.Scheme S1. Synthetic route used to produce 3, I = ferrocenecarboxylic acid. Scheme S2. Synthetic methods used to produce 5 and 6 (II = 1'-Fmoc-amino-ferrocene carboxylic acid).

Cited by 5 publications

References 42 publications

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

The Importance of 6-Aminohexanoic Acid as a Hydrophobic, Flexible Structural Element

Ferrocenyl chalcogeno (sugar) triazole conjugates: Synthesis, characterization and anticancer properties

Contact Info

Product

Resources

About