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(9 Z )‐ and (11 Z )‐8‐Methylretinals for artificial visual pigment studies: stereoselective synthesis, structure, and binding models

Identificadores del recurso

Chemistry - A European Journal, 9(23): 5821-5831 (2003)

09476539

15213765

http://hdl.handle.net/11093/8580

10.1002/chem.200304847

https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.200304847

Procedência

Ficha

Título:: (9 Z )‐ and (11 Z )‐8‐Methylretinals for artificial visual pigment studies: stereoselective synthesis, structure, and binding models
Tema:: 2306 Química Orgánica
Descrição:: Artificial visual pigment formation was studied by using 8-methylsubstituted retinals in an effort to understand the effect that alkyl substitution of the chromophore side chain has on the visual cycle. The stereoselective synthesis of the 9-cis and 11-cis isomers of 8-methylretinal, as well as the 5-demethylated analogues is also described. The key bond formations consist of a thallium-accelerated Suzuki cross-coupling reaction between cyclohexenylboronic acids and dienyliodides (C6-C7), and a highly stereocontrolled Horner-Wadsworth-Emmons or Wittig condensation (C11-C12). The cyclohexenylboronic acid was prepared by trapping the precursor cyclohexenyllithium species with B(OiPr)3 or B(OMe)3. The cyclohexenyllithium species is itself obtained by nBuLi-induced elimination of a trisylhydrazone (Shapiro reaction), or depending upon the steric hindrance of the ring, by iodine-metal exchange. In binding experiments with the apoprotein opsin, only 9-cis-5-demethyl-8-methylretinal yielded an artificial pigment; 9-cis-8-methylretinal simply provided residual binding, while evidence of artificial pigment formation was not found for the 11-cis analogues. Molecular-mechanics based docking simulations with the crystal structure of rhodopsin have allowed us to rationalize the lack of binding displayed by the 11-cis analogues. Our results indicate that these isomers are highly strained, especially when bound, due to steric clashes with the receptor, and that these interactions are undoubtedly alleviated when 9-cis-5-demethyl-8-methylretinal binds opsin.; Xunta de Galicia
Idioma:: English
Autor/Produtor:: Álvarez Rodríguez, Maria Rosana; Domínguez Seoane, Marta; Pazos Randulfe, Yolanda; Sussman, Fredy; Rodríguez de Lera, Ángel
Editor:: Chemistry - A European Journal; Química orgánica; Química Orgánica 1
Direitos:: © 2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; closedAccess
Data:: 2025-01-29T11:51:16Z; 2003-12-05; indefinido; 2025-01-28T20:43:55Z
Tipo de recurso:: article

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2. < dc:creator > Álvarez Rodríguez, Maria Rosana </ dc:creator >
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        < mods:namePart > Sussman, Fredy </ mods:namePart >
        
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        < mods:namePart > Rodríguez de Lera, Ángel </ mods:namePart >
        
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        < mods:dateAccessioned encoding =" iso8601 " > 2025-01-29T11:51:16Z </ mods:dateAccessioned >
        
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        < mods:dateIssued encoding =" iso8601 " > 2003-12-05 </ mods:dateIssued >
        
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        < mods:identifier type =" citation " > Chemistry - A European Journal, 9(23): 5821-5831 (2003) </ mods:identifier >
        
        < mods:identifier type =" issn " > 0947653915213765 </ mods:identifier >
        
        < mods:identifier type =" uri " > http://hdl.handle.net/11093/8580 </ mods:identifier >
        
        < mods:identifier type =" doi " > 10.1002/chem.200304847 </ mods:identifier >
        
        < mods:identifier type =" editor " > https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.200304847 </ mods:identifier >
        
        < mods:abstract > Artificial visual pigment formation was studied by using 8-methylsubstituted retinals in an effort to understand the effect that alkyl substitution of the chromophore side chain has on the visual cycle. The stereoselective synthesis of the 9-cis and 11-cis isomers of 8-methylretinal, as well as the 5-demethylated analogues is also described. The key bond formations consist of a thallium-accelerated Suzuki cross-coupling reaction between cyclohexenylboronic acids and dienyliodides (C6-C7), and a highly stereocontrolled Horner-Wadsworth-Emmons or Wittig condensation (C11-C12). The cyclohexenylboronic acid was prepared by trapping the precursor cyclohexenyllithium species with B(OiPr)3 or B(OMe)3. The cyclohexenyllithium species is itself obtained by nBuLi-induced elimination of a trisylhydrazone (Shapiro reaction), or depending upon the steric hindrance of the ring, by iodine-metal exchange. In binding experiments with the apoprotein opsin, only 9-cis-5-demethyl-8-methylretinal yielded an artificial pigment; 9-cis-8-methylretinal simply provided residual binding, while evidence of artificial pigment formation was not found for the 11-cis analogues. Molecular-mechanics based docking simulations with the crystal structure of rhodopsin have allowed us to rationalize the lack of binding displayed by the 11-cis analogues. Our results indicate that these isomers are highly strained, especially when bound, due to steric clashes with the receptor, and that these interactions are undoubtedly alleviated when 9-cis-5-demethyl-8-methylretinal binds opsin. </ mods:abstract >
        
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        < mods:languageTerm authority =" rfc3066 " > eng </ mods:languageTerm >
        
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        < mods:accessCondition type =" useAndReproduction " > © 2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim </ mods:accessCondition >
        
        < mods:titleInfo >
        
        < mods:title > (9 Z )‐ and (11 Z )‐8‐Methylretinals for artificial visual pigment studies: stereoselective synthesis, structure, and binding models </ mods:title >
        
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7. < dcterms:abstract > Artificial visual pigment formation was studied by using 8-methylsubstituted retinals in an effort to understand the effect that alkyl substitution of the chromophore side chain has on the visual cycle. The stereoselective synthesis of the 9-cis and 11-cis isomers of 8-methylretinal, as well as the 5-demethylated analogues is also described. The key bond formations consist of a thallium-accelerated Suzuki cross-coupling reaction between cyclohexenylboronic acids and dienyliodides (C6-C7), and a highly stereocontrolled Horner-Wadsworth-Emmons or Wittig condensation (C11-C12). The cyclohexenylboronic acid was prepared by trapping the precursor cyclohexenyllithium species with B(OiPr)3 or B(OMe)3. The cyclohexenyllithium species is itself obtained by nBuLi-induced elimination of a trisylhydrazone (Shapiro reaction), or depending upon the steric hindrance of the ring, by iodine-metal exchange. In binding experiments with the apoprotein opsin, only 9-cis-5-demethyl-8-methylretinal yielded an artificial pigment; 9-cis-8-methylretinal simply provided residual binding, while evidence of artificial pigment formation was not found for the 11-cis analogues. Molecular-mechanics based docking simulations with the crystal structure of rhodopsin have allowed us to rationalize the lack of binding displayed by the 11-cis analogues. Our results indicate that these isomers are highly strained, especially when bound, due to steric clashes with the receptor, and that these interactions are undoubtedly alleviated when 9-cis-5-demethyl-8-methylretinal binds opsin. </ dcterms:abstract >
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  7. < dc:description > Artificial visual pigment formation was studied by using 8-methylsubstituted retinals in an effort to understand the effect that alkyl substitution of the chromophore side chain has on the visual cycle. The stereoselective synthesis of the 9-cis and 11-cis isomers of 8-methylretinal, as well as the 5-demethylated analogues is also described. The key bond formations consist of a thallium-accelerated Suzuki cross-coupling reaction between cyclohexenylboronic acids and dienyliodides (C6-C7), and a highly stereocontrolled Horner-Wadsworth-Emmons or Wittig condensation (C11-C12). The cyclohexenylboronic acid was prepared by trapping the precursor cyclohexenyllithium species with B(OiPr)3 or B(OMe)3. The cyclohexenyllithium species is itself obtained by nBuLi-induced elimination of a trisylhydrazone (Shapiro reaction), or depending upon the steric hindrance of the ring, by iodine-metal exchange. In binding experiments with the apoprotein opsin, only 9-cis-5-demethyl-8-methylretinal yielded an artificial pigment; 9-cis-8-methylretinal simply provided residual binding, while evidence of artificial pigment formation was not found for the 11-cis analogues. Molecular-mechanics based docking simulations with the crystal structure of rhodopsin have allowed us to rationalize the lack of binding displayed by the 11-cis analogues. Our results indicate that these isomers are highly strained, especially when bound, due to steric clashes with the receptor, and that these interactions are undoubtedly alleviated when 9-cis-5-demethyl-8-methylretinal binds opsin. </ dc:description >
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10. < dcterms:abstract lang =" en " > Artificial visual pigment formation was studied by using 8-methylsubstituted retinals in an effort to understand the effect that alkyl substitution of the chromophore side chain has on the visual cycle. The stereoselective synthesis of the 9-cis and 11-cis isomers of 8-methylretinal, as well as the 5-demethylated analogues is also described. The key bond formations consist of a thallium-accelerated Suzuki cross-coupling reaction between cyclohexenylboronic acids and dienyliodides (C6-C7), and a highly stereocontrolled Horner-Wadsworth-Emmons or Wittig condensation (C11-C12). The cyclohexenylboronic acid was prepared by trapping the precursor cyclohexenyllithium species with B(OiPr)3 or B(OMe)3. The cyclohexenyllithium species is itself obtained by nBuLi-induced elimination of a trisylhydrazone (Shapiro reaction), or depending upon the steric hindrance of the ring, by iodine-metal exchange. In binding experiments with the apoprotein opsin, only 9-cis-5-demethyl-8-methylretinal yielded an artificial pigment; 9-cis-8-methylretinal simply provided residual binding, while evidence of artificial pigment formation was not found for the 11-cis analogues. Molecular-mechanics based docking simulations with the crystal structure of rhodopsin have allowed us to rationalize the lack of binding displayed by the 11-cis analogues. Our results indicate that these isomers are highly strained, especially when bound, due to steric clashes with the receptor, and that these interactions are undoubtedly alleviated when 9-cis-5-demethyl-8-methylretinal binds opsin. </ dcterms:abstract >
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xoai

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