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t-Butyloxycarbonyl: an ordinary but promising group for protecting peptides from deiodination
Xin Sun1, Taiwei Chu, Xinqi Liu
1Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Abstract:
In order to protect directly radioiodinated peptides from in vivo deiodination, a novel procedure was explored. Two peptides, Try-Gly-Gly-Gly-Gly-Gly-Cys-Asn-Gly-Arg-Cys (YG5) and t-Boc-Try-Gly-Gly-Gly-Gly-Gly-Cys-Asn-Gly-Arg-Cys (t-BOC-YG5) were synthesized and radiolabeled. A paired-label biodistribution study using [131I]t-BOC-YG5 and [125I]YG5 was undertaken in normal mice. Compared to [125I]YG5, [131I]t-BOC-YG5 was quite resistant to in vivo deiodination, resulting in rapid reduction of the radioactive background and negligible radioactivity accumulation in both thyroid and stomach. [131I]t-BOC-YG5 was also stable in human serum even after 24 h. In conclusion, the t-BOC group has the potential to protect peptide from deiodination.
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