AsLn2, a luciferin-related modified tripeptide from the bioluminescent earthworm Fridericia heliota

AsLn2, an unusual modified peptide, was isolated from the bioluminescent earthworm Fridericia heliota (Enchytraeidae). Its structure, elucidated by NMR and mass spectrometry, includes residues of tyrosine, CompX (a novel tyrosine modification product, reported in the accompanying paper), and N(omega...

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Bibliographic Details
Published in:Tetrahedron letters 2014-01, Vol.55 (2), p.463-465
Main Authors: Petushkov, Valentin N., Dubinnyi, Maxim A., Rodionova, Natalja S., Nadezhdin, Kirill D., Marques, Simone M., Esteves da Silva, Joaquim C.G., Shimomura, Osamu, Yampolsky, Ilia V.
Format: Article
Language:English
Subjects:
Bioluminescence
Byproducts
Fridericia heliota
Luciferin
Lysine
Modified peptide
Nuclear magnetic resonance
Residues
Similarity
Tetrahedrons
Tyrosine
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Description
Summary:AsLn2, an unusual modified peptide, was isolated from the bioluminescent earthworm Fridericia heliota (Enchytraeidae). Its structure, elucidated by NMR and mass spectrometry, includes residues of tyrosine, CompX (a novel tyrosine modification product, reported in the accompanying paper), and N(omega)-acylated lysine. Chromatography, UV, and 1H NMR data imply a close structural similarity of AsLn2 with F. heliota luciferin. AsLn2 appears to be an intermediate or by-product in F. heliota luciferin biosynthesis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.11.061