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磷酸化视黄酸的化学合成。它们在大鼠肝细胞膜中的甘露糖基受体活性。

Chemical synthesis of phosphorylated retinoids. Their mannosyl acceptor activity in rat liver membranes.

作者信息

De Luca L M, Frot-Coutaz J P, Silverman-Jones C S, Roller P R

出版信息

J Biol Chem. 1977 Apr 25;252(8):2575-9.

PMID:856793
Abstract

Phosphorylated retinoids were synthesized by a modification of the procedure that Popják et al. (Popják, G., Cornforth, J. W., Cornforth, R. H., Ryhage, R., and Goodman, D. S. (1962) J. Biol. Chem. 237, 56-61) used to synthesize farnesylpyrophosphate. The all-trans-beta-retinyl phosphate; all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraene-1-yl phosphate; perhydromonoeneretinyl phosphate; all-trans-beta-retinoyl phosphate; 13-cis-beta-retinoyl phosphate derivatives were tested as acceptors of [14C]mannose from GDP-[14C]mannose in a reaction catalyzed by rat liver membranes. The phosphate esters all functioned as acceptors of mannose to give a product chromatographically indistinguishable from endogenous mannosylretinyl phosphate. The mixed anhydrides, however, did not function as mannosyl acceptors. Neither class of compounds had any effect on the biosynthesis of dolichylmannosyl phosphate. Rat liver membranes did not catalyze the transfer of [14C]galactose from UDP-[14C]galactose to retinyl phosphate even at a concentration of retinyl phosphate (0.73 mM) which stimulated formation o mannosylretinyl phosphate by more than 50-fold...

摘要

磷酸化视黄醇通过对Popják等人（Popják, G., Cornforth, J. W., Cornforth, R. H., Ryhage, R., and Goodman, D. S. (1962) J. Biol. Chem. 237, 56 - 61）用于合成法呢基焦磷酸的方法进行改进来合成。全反式-β-视黄醇磷酸酯；全反式-9-(4-甲氧基-2,3,6-三甲基苯基)-3,7-二甲基-2,4,6,8-壬四烯-1-基磷酸酯；全氢单烯视黄醇磷酸酯；全反式-β-视黄酰磷酸酯；13-顺式-β-视黄酰磷酸酯衍生物在大鼠肝细胞膜催化的反应中作为GDP-[14C]甘露糖中[14C]甘露糖的受体进行了测试。这些磷酸酯均作为甘露糖的受体，产生一种在色谱上与内源性甘露糖基视黄醇磷酸酯无法区分的产物。然而，混合酸酐并不作为甘露糖基受体起作用。这两类化合物对磷酸多萜醇甘露糖的生物合成均无任何影响。即使在视黄醇磷酸酯浓度为0.73 mM（该浓度能使甘露糖基视黄醇磷酸酯的形成增加50倍以上）时，大鼠肝细胞膜也不催化UDP-[14C]半乳糖中[14C]半乳糖向视黄醇磷酸酯的转移……

相似文献

1
Chemical synthesis of phosphorylated retinoids. Their mannosyl acceptor activity in rat liver membranes.磷酸化视黄酸的化学合成。它们在大鼠肝细胞膜中的甘露糖基受体活性。
J Biol Chem. 1977 Apr 25;252(8):2575-9.
2
Effects of exogenous retinol and retinoic acid on the biosynthesis of 14C-mannose labelled glycolipids and glycoproteins in rat liver.外源性视黄醇和视黄酸对大鼠肝脏中14C-甘露糖标记糖脂和糖蛋白生物合成的影响。
J Nutr Sci Vitaminol (Tokyo). 1978;24(1):9-23. doi: 10.3177/jnsv.24.9.
3
Rat liver microsomes catalyse mannosyl transfer from GDP-D-mannose to retinyl phosphate with high efficiency in the absence of detergents.在没有去污剂的情况下，大鼠肝脏微粒体能够高效催化从GDP-D-甘露糖到磷酸视黄酯的甘露糖基转移反应。
Biochem J. 1981 Dec 15;200(3):529-38. doi: 10.1042/bj2000529.
4
Mannosylation of endogenous and exogenous phosphatidic acid by liver microsomal membranes. Formation of phosphatidylmannose.肝微粒体膜对内源性和外源性磷脂酸的甘露糖基化作用。磷脂酰甘露糖的形成。
J Biol Chem. 1986 Mar 15;261(8):3490-500.
5
Enzymatic synthesis of mannosyl retinyl phosphate from retinyl phosphate and guanosine diphosphate mannose.由磷酸视黄酯和二磷酸鸟苷甘露糖通过酶促合成甘露糖基视黄基磷酸酯。
J Lipid Res. 1975 May;16(3):235-43.
6
The polyenic system of retinyl phosphate is required for its mannosyl donor activity but not for acceptor activity.视黄基磷酸酯的多烯系统是其甘露糖基供体活性所必需的，但对受体活性并非必需。
Biochem J. 1982 Dec 15;208(3):865-8. doi: 10.1042/bj2080865.
7
Transfer of mannose from mannosyl retinyl phosphate to protein.甘露糖从磷酸甘露糖视黄酯向蛋白质的转移。
Proc Natl Acad Sci U S A. 1977 Sep;74(9):3762-6. doi: 10.1073/pnas.74.9.3762.
8
Mannosyl carrier functions of retinyl phosphate and dolichyl phosphate in rat liver endoplasmic reticulum.视黄基磷酸酯和多萜醇磷酸酯在大鼠肝脏内质网中的甘露糖基载体功能
Biochem J. 1983 Feb 15;210(2):541-7. doi: 10.1042/bj2100541.
9
The anomeric configuration of the D-mannosyl retinyl phosphate formed in rat liver microsomes.大鼠肝脏微粒体中形成的D-甘露糖基视黄基磷酸酯的异头构型。
J Biol Chem. 1976 Oct 25;251(20):6465-7.
10
Recent studies on the involvement of retinyl phosphate as a carrier of mannose in biological membranes.近期关于磷酸视黄酯作为甘露糖在生物膜中的载体所起作用的研究。
Ann N Y Acad Sci. 1981 Feb 27;359:345-57. doi: 10.1111/j.1749-6632.1981.tb12759.x.

引用本文的文献

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Involvement of a lipid-linked intermediate in the transfer of galactose from UDP [(14)C]galactose to exogenous protein in castor bean endosperm homogenates.在蓖麻籽胚乳匀浆中外源蛋白上的半乳糖从 UDP [(14)C]半乳糖转移到蛋白的过程中涉及一个脂连接中间产物。
Planta. 1979 Oct;147(1):89-96. doi: 10.1007/BF00384596.
2
Retinoic acid. Inhibition of the clonal growth of human myeloid leukemia cells.维甲酸。对人髓系白血病细胞克隆生长的抑制作用。
J Clin Invest. 1982 Feb;69(2):277-83. doi: 10.1172/jci110450.
3
The polyenic system of retinyl phosphate is required for its mannosyl donor activity but not for acceptor activity.
视黄基磷酸酯的多烯系统是其甘露糖基供体活性所必需的，但对受体活性并非必需。
Biochem J. 1982 Dec 15;208(3):865-8. doi: 10.1042/bj2080865.
4
Topology of UDP-galactose cleavage in relation to N-acetyl-lactosamine formation in Golgi vesicles. Translocation of activated galactose.高尔基体囊泡中UDP-半乳糖裂解的拓扑结构与N-乙酰乳糖胺形成的关系。活化半乳糖的转运。
Biochem J. 1985 Jan 1;225(1):67-75. doi: 10.1042/bj2250067.
5
Altered processing of a major secreted phosphoprotein correlates with tumorigenicity in Rous sarcoma virus-transformed mammalian cells.一种主要分泌磷蛋白的加工改变与劳氏肉瘤病毒转化的哺乳动物细胞中的致瘤性相关。
J Virol. 1985 Mar;53(3):841-50. doi: 10.1128/JVI.53.3.841-850.1985.
6
Synthesis of retinyl phosphate mannose in vitro. Non-enzymic breakdown and reversibility.体外视黄基磷酸甘露糖的合成。非酶促分解与可逆性。
Biochem J. 1985 May 1;227(3):695-703. doi: 10.1042/bj2270695.