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Color regulation and stabilization of chromophore by Cys69 in photoactive yellow protein active center.
Org Biomol Chem. 2009 Sep 21; 7(18):3782-91.OB

Abstract

Model compounds of PYP chromophore were synthesized and characterized to investigate the role of the Cys69 residue in the active center, which has the intramolecular NHOC hydrogen bond to the conjugated carbonyl oxygen and thioester linkage of the chromophore. The results of UV-vis and (13)C NMR spectroscopy of the model compounds indicated that they delocalized the negative charge of the chromophore and increased the contribution of the quinoid-like resonance structure in the phenolate anion state. Thus, the Cys69 residue plays an important role in the regulation of the color and the stabilization of the chromophore anion in the active center.

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Authors+Show Affiliations

Okamoto K
Department of Macromolecular Science, Graduate School of Science, Osaka University, Machikaneyama-cho 1-1, Toyonaka, Osaka 560-0043, Japan.
Hamada N
No affiliation info available
Okamura TA
No affiliation info available
Ueyama N
No affiliation info available
Yamamoto H
No affiliation info available

MeSH

AbsorptionBacterial ProteinsColorCysteineEstersHalorhodospira halophilaHydrogen BondingMagnetic Resonance SpectroscopyModels, MolecularMolecular ConformationPhotoreceptors, MicrobialProtein StabilitySpectrophotometry, UltravioletSulfur

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19707683

Citation

Okamoto, Kentaro, et al. "Color Regulation and Stabilization of Chromophore By Cys69 in Photoactive Yellow Protein Active Center." Organic & Biomolecular Chemistry, vol. 7, no. 18, 2009, pp. 3782-91.
Okamoto K, Hamada N, Okamura TA, et al. Color regulation and stabilization of chromophore by Cys69 in photoactive yellow protein active center. Org Biomol Chem. 2009;7(18):3782-91.
Okamoto, K., Hamada, N., Okamura, T. A., Ueyama, N., & Yamamoto, H. (2009). Color regulation and stabilization of chromophore by Cys69 in photoactive yellow protein active center. Organic & Biomolecular Chemistry, 7(18), 3782-91. https://doi.org/10.1039/b905835d
Okamoto K, et al. Color Regulation and Stabilization of Chromophore By Cys69 in Photoactive Yellow Protein Active Center. Org Biomol Chem. 2009 Sep 21;7(18):3782-91. PubMed PMID: 19707683.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Color regulation and stabilization of chromophore by Cys69 in photoactive yellow protein active center. AU - Okamoto,Kentaro, AU - Hamada,Norio, AU - Okamura,Taka-aki, AU - Ueyama,Norikazu, AU - Yamamoto,Hitoshi, Y1 - 2009/07/15/ PY - 2009/8/27/entrez PY - 2009/8/27/pubmed PY - 2009/11/6/medline SP - 3782 EP - 91 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 7 IS - 18 N2 - Model compounds of PYP chromophore were synthesized and characterized to investigate the role of the Cys69 residue in the active center, which has the intramolecular NHOC hydrogen bond to the conjugated carbonyl oxygen and thioester linkage of the chromophore. The results of UV-vis and (13)C NMR spectroscopy of the model compounds indicated that they delocalized the negative charge of the chromophore and increased the contribution of the quinoid-like resonance structure in the phenolate anion state. Thus, the Cys69 residue plays an important role in the regulation of the color and the stabilization of the chromophore anion in the active center. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/19707683/Color_regulation_and_stabilization_of_chromophore_by_Cys69_in_photoactive_yellow_protein_active_center_ L2 - https://doi.org/10.1039/b905835d DB - PRIME DP - Unbound Medicine ER -