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Novel Peptide Chemistry in Terrestrial Animals: Natural Luciferin Analogues from the Bioluminescent Earthworm Fridericia heliota
Author(s) -
Dubinnyi Maxim A.,
Tsarkova Aleksandra S.,
Petushkov Valentin N.,
Kaskova Zinaida M,
Rodionova Natalja S.,
Kovalchuk Sergey I.,
Ziganshin Rustam H.,
Baranov Mikhail S.,
Mineev Konstantin S.,
Yampolsky Ilia V.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406498
Subject(s) - bioluminescence , luciferin , chemistry , peptide , amino acid , earthworm , biochemistry , tyrosine , cysteine , stereochemistry , luciferase , biology , ecology , enzyme , transfection , gene
We report isolation and structure elucidation of AsLn5, AsLn7, AsLn11 and AsLn12: novel luciferin analogs from the bioluminescent earthworm Fridericia heliota . They were found to be highly unusual modified peptides, comprising either of the two tyrosine‐derived chromophores, CompX or CompY and a set of amino acids, including threonine, gamma‐aminobutyric acid, homoarginine, and unsymmetrical N , N ‐dimethylarginine. These natural compounds represent a unique peptide chemistry found in terrestrial animals and rise novel questions concerning their biosynthetic origin.