A Polar F-18-Labeled Amino Acid Derivative for Click Labeling of Biomolecules

作者：Schieferstein Hanno; Ross Tobias L^*

来源：European Journal of Organic Chemistry, 2014, 2014(17): 3546-3550.

DOI：10.1002/ejoc.201400071

• Isotopic labeling
• Amino acids
• Click chemistry
• Molecular imaging
• Diagnostic agents

This work describes the synthesis and F-18-labeling of an amino acid based prosthetic group that is able to participate in copper(I)-catalyzed cycloadditions. The prosthetic group can be used for F-18 labeling of biomolecules under mild conditions. The synthesis started with L-serine methyl ester, which was derivatized by introducing an alkyne moiety and a leaving group for F-18 labeling. Subsequently, F-18 labeling as well as deprotection conditions were screened, which resulted in an overall radiochemical yield (RCY) of around 28%. Furthermore, the F-18-labeled prosthetic group was treated with an azido cyclic Arg-Gly-Asp (cRGD) peptide as a model system in very high RCY of 98%.

• 出版日期2014-6