Fmoc-based solid-phase synthesis of adenylylated peptides using diester-type adenylylated amino acid derivatives |
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Authors: | Keiji OguraAkira Shigenaga Koji EbisunoHiroko Hirakawa Akira Otaka |
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Institution: | Institute of Health Bioscience and Graduate School of Pharmaceutical Sciences, The University of Tokushima, Tokushima 770-8505, Japan |
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Abstract: | Phosphodiester-type adenylylated (AMPylated) Ser, Thr, and Tyr derivatives were developed for Fmoc solid phase peptide synthesis of AMPylated peptides. One-pot/sequential reaction consisting of condensation of an N-nonprotected adenosine derivative and Fmoc-Ser/Thr/Tyr-OAllyl using allyl-N,N-diisopropylchlorophosphoramidite and subsequent oxidation with m-chloroperbenzoic acid gave phosphotriester-type AMPylated Ser/Thr/Tyr derivatives. After Pd(0)-mediated deprotection of allyl groups, the resulting phosphodiester-type AMPylated Ser/Thr/Tyr derivatives were successfully incorporated into peptides by standard Fmoc solid phase peptide synthesis without significant side reactions including dehydroalanine formation. |
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Keywords: | AMPylation AMPylated amino acid Phosphodiester amino acid Phosphoramidite method Fmoc solid-phase peptide synthesis |
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