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Chemical synthesis of all-trans-beta-retinoyl phosphat.全反式-β-视黄酰磷脂的化学合成
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2
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本文引用的文献

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THE BIOLOGICAL FUNCTION OF VITAMIN A ACID.视黄酸的生物学功能
Proc Natl Acad Sci U S A. 1960 May;46(5):587-608. doi: 10.1073/pnas.46.5.587.
2
Studies on the biosynthesis of cholesterol. XVI. Chemical synthesis of 1-H2-3-2-C-14- and 1-D2-2-C-14-trans-trans-farnesyl pyrophosphate and their utilization in squalene biosynthesis.胆固醇生物合成的研究。十六。1-H₂-3-²C-¹⁴-和1-D₂-2-²C-¹⁴-反式-反式-法呢基焦磷酸的化学合成及其在角鲨烯生物合成中的应用。
J Biol Chem. 1962 Jan;237:56-61.
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A simple method for the isolation and purification of total lipides from animal tissues.一种从动物组织中分离和纯化总脂质的简单方法。
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4
Changes in the tissues of guinea-pigs fed on a diet free from vitamin A but containing methyl retinoate.以不含维生素A但含有甲基视黄酸的饮食喂养的豚鼠组织变化。
Br J Nutr. 1967;21(1):37-44. doi: 10.1079/bjn19670007.
5
Studies on metabolism of vitamin A. The effect of hormones on gestation in retinoate-fed female rats.维生素A代谢研究。激素对喂食视黄酸的雌性大鼠妊娠的影响。
Biochem J. 1969 Jan;111(1):97-105. doi: 10.1042/bj1110097.
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Biosynthesis of a fucose-containing glycopeptide from rat small intestine in normal and vitamin A-deficient conditions.
J Biol Chem. 1970 Sep 10;245(17):4551-8.
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The biosynthesis of a mannolipid that contains a polar metabolite of 15-14C-retinol.
Biochem Biophys Res Commun. 1970 Nov 9;41(3):615-20. doi: 10.1016/0006-291x(70)90057-4.
8
Retinol glycolipids.视黄醇糖脂
J Biol Chem. 1973 Jan 25;248(2):641-8.
9
Localization of the retinol-dependent fucose-glycopeptide in the goblet cell of the rat small intestine.视黄醇依赖性岩藻糖糖肽在大鼠小肠杯状细胞中的定位。
J Biol Chem. 1971 Sep 25;246(18):5762-5.
10
Biosynthetic studies on mannolipids and mannoproteins of normal and vitamin A-depleted hamster livers.
Biochim Biophys Acta. 1975 Dec 17;409(3):342-59. doi: 10.1016/0005-2760(75)90030-2.

全反式-β-视黄酰磷脂的化学合成

Chemical synthesis of all-trans-beta-retinoyl phosphat.

作者信息

Frot-Coutaz J P, de Luca L M

出版信息

Biochem J. 1976 Dec 1;159(3):799-801. doi: 10.1042/bj1590799.

DOI:10.1042/bj1590799
PMID:1008836
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1164184/
Abstract

all-trans-beta-Retinoic acid is phosphorylated to retinoyl phosphate by bis(triethylamine) phosphate with yields of 10-15%. The product is soluble in methanol and is eluted from DEAE-cellulose acetate at a concentration of 0.1M-ammonium acetate in 99% (v/v) methanol. Its phosphate/retinoic acid molar ratio is 1. Retinoyl phosphate has an absorption maximum at 360nm in methanol, whereas retinoic acid has a maximum at 350 nm. The compound is hydrolysed at pH2 and pH13 for 20 min at 37 degrees C, but is relatively stable under the same conditions at pH4, 6, 8 and 10. Retinoyl phosphate (RF 0.1) can be separated from retinyl phosphate (RF 0.2) by chromatography on thin layers of silica gel in chloroform/methanol/water (60:25:4, by vol.).

摘要

全反式-β-视黄酸通过磷酸双(三乙胺)磷酸化生成视黄酰磷酸,产率为10 - 15%。产物可溶于甲醇,并在99%(v/v)甲醇中0.1M醋酸铵浓度下从DEAE - 醋酸纤维素上洗脱下来。其磷酸/视黄酸摩尔比为1。视黄酰磷酸在甲醇中的最大吸收波长为360nm,而视黄酸的最大吸收波长为350nm。该化合物在pH2和pH13、37℃下20分钟会水解,但在pH4、6、8和10的相同条件下相对稳定。视黄酰磷酸(比移值0.1)可通过在硅胶薄层上用氯仿/甲醇/水(60:25:4,体积比)进行色谱分离与视黄基磷酸(比移值0.2)分离。