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α‐C‐Mannosyltryptophan is a Structural Analog of the Luciferin from Bioluminescent Siberian Earthworm Henlea sp .
Author(s) -
Dubinnyi Maxim A.,
Ivanov Igor A.,
Rodionova Natalia S.,
Kovalchuk Sergey I.,
Kaskova Zinaida M.,
Petushkov Valentin N.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003075
Subject(s) - bioluminescence , luciferin , earthworm , chemistry , stereochemistry , biochemistry , tryptophan , photoprotein , luciferase , biology , ecology , transfection , amino acid , gene
Cold extract from bioluminescent earthworm Henlea sp . was studied by HPLC, 1D and 2D NMR and LC‐HRMS analysis. An abundant structural analog of the luciferin was isolated and identified as α‐C‐mannosyltryptophan (ManTrp), the product of unusual C2‐glycosylation found earlier in humans, ascidians and other animals. Two compounds in cold extract (P300b, P300c) were characterized as C2‐substituted derivatives of tryptophan. We hypothesize that a series of tryptophan‐containing compounds are possible participants of bioluminescence‐related metabolism in Henlea sp .