Synthesis of Anabaenopeptins With a Strategic Eye Toward N-Terminal Sequence Diversity.

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Tác giả: Dennis P Anderson, Zoee K Harris, Sydney C Kasmer, Nicholas J Peraino, Boddu S Ramakrishna, Jennifer L Stockdill, Naresh M Venneti, Judy A Westrick

Ngôn ngữ: eng

Ký hiệu phân loại:

Thông tin xuất bản: England : Journal of peptide science : an official publication of the European Peptide Society , 2025

Mô tả vật lý:

Bộ sưu tập: NCBI

ID: 701873

A divergent synthesis strategy was developed for producing various anabaenopeptins (AP) for harmful algal bloom monitoring. The synthesis involved on-resin stepwise pentapeptide assembly on a MeDbz linker then N-α-ureido amino acid attachment and cyclization. To manage N-methylated amino acids, modified coupling conditions were employed. Lysine's ε-amino group reacted with the activated MeDbz linker in a self-cleaving head-to-side chain cyclization. Cyclization conditions were optimized by screening different pH levels to control lysine α-amine cyclization and prevent hydrolysis. Global cleavage and purification afforded the pure anabaenopeptins. This approach proved effective as a general platform for anabaenopeptin synthesis, allowing rapid access to anabaenopeptins A, B, F, and oscillamide Y.
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