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全反式视黄醛在体外异构化为11-顺式视黄醛。

Isomerization of all-trans-retinoids to 11-cis-retinoids in vitro.

作者信息

Bernstein P S, Law W C, Rando R R

出版信息

Proc Natl Acad Sci U S A. 1987 Apr;84(7):1849-53. doi: 10.1073/pnas.84.7.1849.

DOI:10.1073/pnas.84.7.1849
PMID:3494246
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC304538/
Abstract

The key biochemical process of the vertebrate visual cycle required for rhodopsin regeneration, 11-cis-retinoid production from all-trans-retinoids, is shown to occur in vitro. A 600 X g supernatant from a frog retina/pigment epithelium homogenate transforms added all-trans-[3H]retinol, in a time-dependent fashion, to a mixture of 11-cis-retinol, 11-cis-retinal, and 11-cis-retinyl palmitate. 13-cis-Retinoids are formed in only minor amounts by nonspecific processes. Studies using washed particulate fractions of the 600 X g supernatant indicate that all-trans-[3H]retinol is isomerized to 11-cis-retinoids much more effectively than is all-trans-[3H]retinal or all-trans-[3H]retinyl palmitate. The 11-cis-retinoid biosynthetic activity is heat-labile, sedimentable by high-speed centrifugation, and largely found in the pigment epithelium rather than in the neural retina.

摘要

视紫红质再生所需的脊椎动物视觉循环的关键生化过程,即从全反式视黄醛生成11-顺式视黄醛,已证实在体外可以发生。青蛙视网膜/色素上皮匀浆的600×g上清液能将添加的全反式-[3H]视黄醇以时间依赖性方式转化为11-顺式视黄醇、11-顺式视黄醛和11-顺式视黄醇棕榈酸酯的混合物。13-顺式视黄醛仅通过非特异性过程少量形成。使用600×g上清液的洗涤颗粒部分进行的研究表明,全反式-[3H]视黄醇异构化为11-顺式视黄醛的效率远高于全反式-[3H]视黄醛或全反式-[3H]视黄醇棕榈酸酯。11-顺式视黄醛生物合成活性对热不稳定,可通过高速离心沉淀,并且主要存在于色素上皮中而非神经视网膜中。

相似文献

1
Isomerization of all-trans-retinoids to 11-cis-retinoids in vitro.全反式视黄醛在体外异构化为11-顺式视黄醛。
Proc Natl Acad Sci U S A. 1987 Apr;84(7):1849-53. doi: 10.1073/pnas.84.7.1849.
2
In vivo isomerization of all-trans- to 11-cis-retinoids in the eye occurs at the alcohol oxidation state.眼睛中全反式视黄醛向11-顺式视黄醛的体内异构化发生在醇氧化态。
Biochemistry. 1986 Oct 21;25(21):6473-8. doi: 10.1021/bi00369a020.
3
Visual cycle in the mammalian eye. Retinoid-binding proteins and the distribution of 11-cis retinoids.哺乳动物眼中的视觉循环。类视黄醇结合蛋白与11-顺式视黄醇的分布。
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Stereochemical inversion at C-15 accompanies the enzymatic isomerization of all-trans- to 11-cis-retinoids.C-15位的立体化学反转伴随着全反式视黄醛向11-顺式视黄醛的酶促异构化过程。
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Utilization of exogenous retinol by frog pigment epithelium.青蛙色素上皮对外源视黄醇的利用
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Biochemical characterization of the retinoid isomerase system of the eye.眼部类视黄醇异构酶系统的生化特性
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All-trans-retinyl esters are the substrates for isomerization in the vertebrate visual cycle.全反式视黄酯是脊椎动物视觉循环中异构化反应的底物。
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本文引用的文献

1
Retinene isomerase.视黄醛异构酶
J Gen Physiol. 1956 Jul 20;39(6):935-62. doi: 10.1085/jgp.39.6.935.
2
Cis-trans isomers of vitamin A and retinene in the rhodopsin system.视紫红质系统中维生素A和视黄醛的顺反异构体。
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Enzymatic esterification of vitamin A in the pigment epithelium of bovine retina.牛视网膜色素上皮中维生素A的酶促酯化作用。
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Measurement of the vitamin A cycle.维生素A循环的测量。
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Vitamin A in human eyes: amount, distribution, and composition.人眼中的维生素A:含量、分布及组成
Invest Ophthalmol Vis Sci. 1982 Jun;22(6):706-14.
6
Enzymatic reduction of 11-cis-retinal bound to cellular retinal-binding protein.与细胞视黄醛结合蛋白结合的11-顺式视黄醛的酶促还原作用。
Biochim Biophys Acta. 1982 May 27;716(2):266-72. doi: 10.1016/0304-4165(82)90277-x.
7
Photolyzed rhodopsin catalyzes the exchange of GTP for bound GDP in retinal rod outer segments.光解视紫红质催化视网膜杆状细胞外段中GTP与结合的GDP的交换。
Proc Natl Acad Sci U S A. 1980 May;77(5):2500-4. doi: 10.1073/pnas.77.5.2500.
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Vitamin A utilization in human retinal pigment epithelial cells in vitro.维生素A在人视网膜色素上皮细胞中的体外利用
Invest Ophthalmol Vis Sci. 1983 Sep;24(9):1227-35.
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Statistical solvent optimization for the separation of geometric isomers of retinol by high-performance liquid chromatography.用于通过高效液相色谱法分离视黄醇几何异构体的统计溶剂优化
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Utilization of exogenous retinol by frog pigment epithelium.青蛙色素上皮对外源视黄醇的利用
Vision Res. 1983;23(1):47-52. doi: 10.1016/0042-6989(83)90040-8.