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Structure Revision of Protoaculeine B, a Posttranslationally Modified N-Terminal Residue in the Peptide Toxin Aculeine B

preprint
submitted on 08.10.2020 and posted on 08.10.2020 by Raku Irie, Kei Miyako, Satoko Matsunaga, Ryuichi Sakai, Masato Oikawa
Here, we newly propose the structure of protoaculeine B, an N-terminal moiety of the marine peptide toxin aculeine B, as possessing the cis-disubstituted tetrahydro-beta-carboline framework. We prepared two truncated model compounds that lack long-chain polyamine by one-step Pictet-Spengler reaction of tryptophan, and compared the NMR and mass spectra and chemical reactivity with those of natural protoaculeine B. The synthetic models reproduced the profiles of the natural product well, which was conclusive for the structural revision.

Funding

The grant for 2020 Research Development Fund of Yokohama City University, Japan

The JSPS grant-in-aid for scientific research (15H04546, 19H03040)

History

Email Address of Submitting Author

moikawa@yokohama-cu.ac.jp

Institution

Yokohama City University

Country

Japan

ORCID For Submitting Author

0000-0002-3919-811X

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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