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Polytheonamides A and B, Highly Cytotoxic, Linear Polypeptides with Unprecedented Structural Features, from the Marine Sponge, Theonella s winhoei

Hamada, Toshiyuki, Matsunaga, Shigeki, Yano, Gen, Fusetani, Nobuhiro·2005·Journal of the American Chemical Society
DOI 10.1021/ja045749e
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Abstract

Polytheonamides A and B are highly cytotoxic polypeptides with 48 amino acid residues isolated from the marine sponge, Theonella swinhoei. The structure of polytheonamide B was determined by spectral and chemical methods, especially extensive 2D NMR experiments, which resulted in the unprecedented polypeptide structure; the N-terminal glycine blocked with a 5,5-dimethyl-2-oxo-hexanoyl group, the presence of eight tert-leucine, three beta-hydroxyvaline, six gamma-N-methylasparagine, two gamma-N-methyl-beta-hydroxyasparagine, and beta,beta-dimethymethionine sulfoxide residues. More significantly, it has the sequence of alternating D- and L-amino acids. Polytheonamide A is an epimer of polytheonamide B differing only in the stereochemistry of the sulfoxide of the 44(th) residue.

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Metadata

Authors
Hamada, T., Matsunaga, S., Yano, G., & Fusetani, N.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2004-12-13
Volume
127
Issue
1
Pages
110-118
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja045749e
OpenAlex
W2092926254
Cited by
211
References
0
FWCI
2.49
Type
journal article
Language
en
Open access
closed

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