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902314

Sigma-Aldrich

[CpRu(Fmoc-tyrosin)]CF3CO2

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Synonym(s):
Fmoc-protected ruthenium tyrosine amino acid derivative, Peptide radiolabel precursor, [18F]Fluorophenylalanine peptide residue precursor
Empirical Formula (Hill Notation):
C31H26F3NO7Ru
Molecular Weight:
682.61
NACRES:
NA.26

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

mp

>300 °C

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

O[C]1[CH][CH][C](CC(NC(OCC2C(C=CC=C3)=C3C4=C2C=CC=C4)=O)C(O)=O)[CH][CH]1.F[C-](F)F.O=C=O.[Ru+].c5cccc5

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Application

The Ritter lab has developed a new method for direct labeling of polypeptides with the [18F]fluoride radiolabel. This Fmoc-protected ruthenium tyrosine is first incorporated into peptides, which is amenable to standard solid-phase peptide synthesis (SPPS) and is tolerant of all 20 canonical amino acids. Subsequent replacement of a single hydrogen with fluorine-18, with only minimal perturbation of the peptide structure, results in a site-specific, radiolabeled peptide tracer for use with positron emission tomography (PET) imaging in the study of various biological applications.

Caution

Research quantities limited to 10 g.

Other Notes

Site-SpecificDeoxyfluorination of Small Peptides with [18F]Fluoride

Legal Information

Patent Application EP18204755.5
This product is manufactured pursuant to a license with Studiengesellschaft Kohle mbH

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Jens Rickmeier et al.
Angewandte Chemie (International ed. in English), 57(43), 14207-14211 (2018-09-07)
Radiolabeled receptor-binding peptides are an important class of positron emission tomography tracers owing to achievable high binding affinities and their rapid blood clearance. Herein, a method to introduce a 4-[18 F]fluoro-phenylalanine residue into peptide sequences is reported, by chemoselective radio-deoxyfluorination

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