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Perfluoro-Tert-Butyl Hydroxyproline

详细技术说明

Development  of new  probes  to detect specific  molecular  events associated  with  disease would  substantially increase theinformation content of MRI. 19F imaging has enormous  potential because of its specificity (highsignal to  noise  due to  the  absence of fluorine in vivo,  itshigh  sensitivity  compared to  proton imaging,   and  its application using commercial proton  magnetic  resonance instruments). The potential of 19F magnetic imagingin  medicine  is currently  substantially limitedby a need to achieve  increased  sensitivity for  applications.  An ideal approach to  enhance specificity  and  sensitivity of  19F  magnetic resonance  spectroscopy would  involve  the incorporation  of  an intense fluorine signal into native ligands in a manner  that is minimally disruptive of structure.This invention incorporates perfluoro-tert-butylgroups, specifically perfluoro-tert-butylhydroxyproline,into  peptides  as novel amino acids. Perfluoro-tert-butylgroups have 9 equivalent  fluorines, andthus have a 9-fold increase in signal-to-noise over  single  fluorines. At least as importantly, perfluoro-tert-butylgroups are sharp  singlets  by NMR, further increasing signal-to-noiseand operational simplicity,  meaning thatmost existing proton-based instrumentation can be readily adjusted to detect peptides containing  perfluoro-tert-butyl  groups. Because  of its highsignal-to-noise ratio and the ability  to  be incorporated  within  peptides and proteins,   perfluoro-tert-butyl   hydroxyproline   has  broad    potential applications inmagnetic imaging (NMR, MRS,  MRI),  both  in  vitro  and  in vivo. Tert-butyl  groups also have  broad  importance in  medicinal chemistry due to theirhydrophobicity  and  symmetry, leading  to  enhanced binding to targets.Fig. Full NMR spectrum of peptide Ac-TYP(4R-OC(CF3)3)N-NH2.

*Abstract

None

*Inquiry

Denise M. BierleinUniversity of DelawareOffice of Economic Innovation and PartnershipsLicensing AnalystTelephone:  (302) 831-4005Email:  deniseb@udel.edu

*IP Issue Date

None

*IP Type

Utility

国家

United States

申请号码

Patent Pending

国家/地区

美国