CompX, a luciferin-related tyrosine derivative from the bioluminescent earthworm Fridericia heliota. Structure elucidation and total synthesis

Valentin N. Petushkov; Aleksandra S. Tsarkova; Maxim A. Dubinnyi

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CompX, a luciferin-related tyrosine derivative from the bioluminescent earthworm Fridericia heliota. Structure elucidation and total synthesis

机译：CompX，来自生物发光earth Fridericia heliota的萤光素相关酪氨酸衍生物。结构阐明和全合成

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A luciferin analog, CompX, was isolated from the extracts of the bioluminescent earthworm Fridericia heliota. Its structure was determined as (Z)-5-(2-carboxy-2-methoxyvinyl)-2-hydroxybenzoic acid by spectroscopic data analysis and was confirmed by total synthesis. The (Z)-configuration of the double bond was established by comparing the ROESY spectra of CompX with those of its synthetic (E)-isomer. CompX represents a tyrosine analog, not previously found in natural sources, and is probably derived from tyrosine by deamination, O-methylation of the resulting alpha-keto acid, and carboxylation at the aromatic core.

机译：从生物发光earthFridericia heliota的提取物中分离出萤光素类似物CompX。通过光谱数据分析确定其结构为（Z）-5-（2-羧基-2-甲氧基乙烯基）-2-羟基苯甲酸，并通过全合成证实。通过比较CompX的ROESY光谱与其合成的（E）异构体的ROESY光谱，可以确定双键的（Z）构型。 CompX代表酪氨酸类似物，以前在天然来源中未发现，并且可能是通过脱氨，所得α-酮酸的O-甲基化以及芳族核心的羧化作用而衍生自酪氨酸的。

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《Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry》 |2014年第2期|共3页
作者
Valentin N. Petushkov; Aleksandra S. Tsarkova; Maxim A. Dubinnyi;
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正文语种 eng
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Bioluminescence; Enchytraeid; Luciferin; Total synthesis;

机译：生物发光;肠磷脂;荧光素;总合成;

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1. CompX, a luciferin-related tyrosine derivative from the bioluminescent earthworm Fridericia heliota. Structure elucidation and total synthesis [J] . Valentin N. Petushkov, Aleksandra S. Tsarkova, Maxim A. Dubinnyi Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2014,第2期

机译：CompX，来自生物发光earth Fridericia heliota的萤光素相关酪氨酸衍生物。结构阐明和全合成
2. Total synthesis of AsLn2-a luciferin analogue from the Siberian bioluminescent earthworm Fridericia heliota [J] . Tsarkova Aleksandra S., Dubinnyi Maxim A., Baranov Mikhail S., Mendeleev Communications . 2015,第2期

机译：西伯利亚生物发光earthFridricia heliota的AsLn2-a荧光素类似物的全合成
3. AsLn2, a luciferin-related modified tripeptide from the bioluminescent earthworm Frideritia heliota [J] . Valentin N. Petushkov, Maxim A. Dubinnyi, Natalja S. Rodionova Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2014,第2期

机译：AsLn2，来自生物发光luminescent Frideritia heliota的萤光素相关修饰三肽
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CompX, a luciferin-related tyrosine derivative from the bioluminescent earthworm Fridericia heliota. Structure elucidation and total synthesis

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