A Novel Strategy for Preparing Glycopeptide Molecular Probe Using Fluorous Technology

Title:A Novel Strategy for Preparing Glycopeptide Molecular Probe Using Fluorous Technology

Volume: 21 Issue: 10

Author(s): Zhiguo Liu, Pengfei Rong, Xiangying Gu, Lun Yu, Guohua Chen, Yue-Lei Chen, Shuai Zhang, Jingkang Shen and Wenbin Zeng

Affiliation:

Keywords: Fluorous technology, glycopeptide, iodination, molecular probe.

Abstract: A novel and convenient strategy for iodine labeled glycopeptide molecular probe and purification was developed. The fluorine rich bi-functional coupling agent, 4-tris(2-perfluorohexylethyl)stannylbenzoate succinimidyl ester, was successfully synthesized via 5 steps starting from the fluorous Grignard reagent. It was purified by a simple and fast isolation using perfluorinated hexanes (FC-72). The “cold” iodine labeled yield for the coupling agent was as high as 92% within 15 min. The iodine-labeled product was only in organic fractions as we expected. It was shown that there was only one major peak in organic fractions according to HPLC. Finally, the iodine-labeled coupling agent was applied to label glycopeptide and afforded a high yield of 87% within 30 min.

Cite this article as:

Liu Zhiguo, Rong Pengfei, Gu Xiangying, Yu Lun, Chen Guohua, Chen Yue-Lei, Zhang Shuai, Shen Jingkang and Zeng Wenbin, A Novel Strategy for Preparing Glycopeptide Molecular Probe Using Fluorous Technology, Protein & Peptide Letters 2014; 21 (10) . https://dx.doi.org/10.2174/0929866521666140626105814