Stereospecificity of retinol saturase: absolute configuration, synthesis, and biological evaluation of dihydroretinoids.
作者信息
Moise Alexander R, Domínguez Marta, Alvarez Susana, Alvarez Rosana, Schupp Michael, Cristancho Ana G, Kiser Philip D, de Lera Angel R, Lazar Mitchell A, Palczewski Krzysztof
机构信息
Department of Pharmacology, Case School of Medicine, Case Western Reserve University, Cleveland, Ohio 44106-4965, USA.
出版信息
J Am Chem Soc. 2008 Jan 30;130(4):1154-5. doi: 10.1021/ja710487q. Epub 2008 Jan 8.
Abstract
摘要
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本文引用的文献
1
Specificity of zebrafish retinol saturase: formation of all-trans-13,14-dihydroretinol and all-trans-7,8- dihydroretinol.斑马鱼视黄醇饱和酶的特异性：全反式-13,14-二氢视黄醇和全反式-7,8-二氢视黄醇的形成。
Biochemistry. 2007 Feb 20;46(7):1811-20. doi: 10.1021/bi062147u. Epub 2007 Jan 25.
2
Metabolism and transactivation activity of 13,14-dihydroretinoic acid.13,14-二氢视黄酸的代谢与反式激活活性
J Biol Chem. 2005 Jul 29;280(30):27815-25. doi: 10.1074/jbc.M503520200. Epub 2005 May 23.
3
Identification of all-trans-retinol:all-trans-13,14-dihydroretinol saturase.全反式视黄醇：全反式-13,14-二氢视黄醇饱和酶的鉴定。
J Biol Chem. 2004 Nov 26;279(48):50230-42. doi: 10.1074/jbc.M409130200. Epub 2004 Sep 9.
4
Vitamin A and the regulation of fat reserves.维生素A与脂肪储备的调节
Cell Mol Life Sci. 2003 Jul;60(7):1311-21. doi: 10.1007/s00018-003-2290-x.
5
Enantiomer discrimination illustrated by high-resolution crystal structures of the human nuclear receptor hRARgamma.人核受体hRARγ的高分辨率晶体结构所示的对映体鉴别
Proc Natl Acad Sci U S A. 2000 Jun 6;97(12):6322-7. doi: 10.1073/pnas.97.12.6322.
6
Identification of highly potent retinoic acid receptor alpha-selective antagonists.高效视黄酸受体α选择性拮抗剂的鉴定。
J Med Chem. 1997 Aug 1;40(16):2445-51. doi: 10.1021/jm9703911.
7
Distinct stages in adipogenesis revealed by retinoid inhibition of differentiation after induction of PPARgamma.在诱导PPARγ后，通过类视黄醇抑制分化揭示脂肪生成的不同阶段。
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8
Characterization of synthetic retinoids with selectivity for retinoic acid or retinoid X nuclear receptors.
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9
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Regional differences in retinoid release from embryonic neural tissue detected by an in vitro reporter assay.通过体外报告基因检测法检测到的胚胎神经组织中类视黄醇释放的区域差异。
Development. 1992 Sep;116(1):55-66. doi: 10.1242/dev.116.1.55.
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