Synthesis of hetero atom modified pyrromethenones

被引：6

作者：

Bongards, Christian ^{[1
]}

Gaertner, Wolfgang ^{[1
]}

机构：

[1] Max Planck Inst Bioinorgan Chem, D-45413 Mulheim An Der Ruhr, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 34期

关键词：

tetrapyrrole chromophore; phytochrome; bilin; phycocyanobilin;

D O I：

10.1002/ejoc.200700656

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of six heteroaromatic compounds, ethyl-/methyl-and dimethylfuranones, thiophenones, and cyclopentenones, was synthesized and condensed with a methyl methylpropionate substituted pyrrole, yielding the "right" half of open-chain tetrapyrroles. These compounds serve as light-inducible chromophores in the plant photoreceptor phytochrome. Three-dimensional structure analysis of the 10-oxapyrromethen-1-one 25 revealed a planar conformation, similar to the dipyrromethenone parent compound, stabilized by a hydrogen bond formed between the pyrrole proton and the furanone oxygen atom. All six pyrrole-substituted heteroaromatic derivatives 25-30 show absorbances in the visible spectrum with high molar extinction coefficients. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：5749 / 5758

页数：10

共 23 条

[1] SILYL NITRONATES IN ORGANIC-SYNTHESIS - ROUTES TO HETEROCYCLES AND CYCLOPENTANOIDS - SYNTHESIS OF ALLETHROLONE AND CALYTHRONE - ACYLATION AND CYANOHYDROXYLATION OF DOUBLE-BONDS - AN EXPLORATORY-STUDY [J].

ANDERSEN, SH ;

DAS, NB ;

JORGENSEN, RD ;

KJELDSEN, G ;

KNUDSEN, JS ;

SHARMA, SC ;

TORSSELL, KBG .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1982, 36 (01) :1-14

[2] BIOSYNTHESIS OF THE TETRAPYRROLE PIGMENT PRECURSOR, DELTA-AMINOLEVULINIC-ACID, FROM GLUTAMATE [J].

BEALE, SI .

PLANT PHYSIOLOGY, 1990, 93 (04) :1273-1279

[3] Dipyrrinones - Constituents of the pigments of life. A review [J].

Boiadjiev, Stefan E. ;

Lightner, David A. .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2006, 38 (04) :347-+

[4] Phytochrome photoconversion [J].

Braslavsky, SE ;

Gartner, W ;

Schaffner, K .

PLANT CELL AND ENVIRONMENT, 1997, 20 (06) :700-706

[5]

CORNEJO J, 1992, J BIOL CHEM, V267, P14790

[6] IMPROVED SYNTHESIS OF PILOCARPINE [J].

DEGRAW, JI .

TETRAHEDRON, 1972, 28 (04) :967-&

[7]

GLAZER AN, 1985, ANNU REV BIOPHYS BIO, V14, P47, DOI 10.1146/annurev.biophys.14.1.47

[8]

GOSSAUER A, 1974, LIEBIGS ANN CHEM, P1496

[9] SYNTHESIS OF BILE-PIGMENTS .7. IMPROVED CHEMICAL SYNTHESIS OF RACEMIC PHYCOCYANOBILIN DIMETHYL ESTER [J].

GOSSAUER, A ;

HINZE, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :283-285

[10] In vitro assembly of phytochrome B apoprotein with synthetic analogs of the phytochrome chromophore [J].

Hanzawa, H ;

Inomata, K ;

Kinoshita, H ;

Kakiuchi, T ;

Jayasundera, KP ;

Sawamoto, D ;

Ohta, A ;

Uchida, K ;

Wada, K ;

Furuya, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (06) :3612-3617

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