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1
N6-Trimethyl-lysine metabolism. 3-Hydroxy-N6-trimethyl-lysine and carnitine biosynthesis.N6-三甲基赖氨酸代谢。3-羟基-N6-三甲基赖氨酸与肉碱的生物合成。
Biochem J. 1980 May 15;188(2):509-19. doi: 10.1042/bj1880509.
2
N6-Trimethyl-lysine metabolism. Structural identification of the metabolite 3-hydroxy-N6-trimethyl-lysine.N6-三甲基赖氨酸代谢。代谢物3-羟基-N6-三甲基赖氨酸的结构鉴定。
Biochem J. 1980 May 15;188(2):521-7. doi: 10.1042/bj1880521.
3
Carnitine biosynthesis. Hydroxylation of N6-trimethyl-lysine to 3-hydroxy-N6-trimethyl-lysine.肉碱生物合成。N6-三甲基赖氨酸羟基化为3-羟基-N6-三甲基赖氨酸。
Biochem J. 1980 May 15;188(2):529-34. doi: 10.1042/bj1880529.
4
Hepatic synthesis of carnitine from protein-bound trimethyl-lysine. Lysosomal digestion of methyl-lysine-labelled asialo-fetuin.从蛋白质结合的三甲基赖氨酸进行肉碱的肝脏合成。甲基赖氨酸标记的去唾液酸胎球蛋白的溶酶体消化。
Biochem J. 1976 Oct 15;160(1):85-95. doi: 10.1042/bj1600085.
5
Biosynthesis of carnitine and 4-N-trimethylaminobutyrate from 6-N-trimethyl-lysine.由N6-三甲基赖氨酸合成肉碱和4-N-三甲基氨基丁酸
Biochem J. 1973 Dec;136(4):1083-90. doi: 10.1042/bj1361083.
6
Biosynthesis of carnitine and 4-N-trimethylaminobutyrate from lysine.由赖氨酸合成肉碱和4-N-三甲基氨基丁酸。
Biochem J. 1973 Dec;136(4):1075-82. doi: 10.1042/bj1361075.
7
Carnitine biosynthesis from gamma-butyrobetaine and from exogenous protein-bound 6-N-trimethyl-L-lysine by the perfused guinea pig liver. Effect of ascorbate deficiency on the in situ activity of gamma-butyrobetaine hydroxylase.豚鼠肝脏灌注实验中γ-丁酰甜菜碱和外源性蛋白质结合的6-N-三甲基-L-赖氨酸的肉碱生物合成。抗坏血酸缺乏对γ-丁酰甜菜碱羟化酶原位活性的影响。
J Biol Chem. 1984 Sep 10;259(17):10764-70.
8
Carnitine biosynthesis in rat and man: tissue specificity.大鼠和人类中肉碱的生物合成：组织特异性。
Nutr Rev. 1981 Jan;39(1):24-6. doi: 10.1111/j.1753-4887.1981.tb06707.x.
9
Carnitine biosynthesis. beta-Hydroxylation of trimethyllysine by an alpha-ketoglutarate-dependent mitochondrial dioxygenase.肉碱的生物合成。由依赖α-酮戊二酸的线粒体双加氧酶对三甲基赖氨酸进行β-羟基化。
J Biol Chem. 1978 Mar 10;253(5):1654-9.
10
The role of the kidney in the biosynthesis of carnitine in the rat.
J Biol Chem. 1979 Nov 10;254(21):10670-4.

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1
Unraveling the metabolomic architecture of autism in a large Danish population-based cohort.在一个大型丹麦基于人群的队列中揭示自闭症的代谢组学结构。
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Trimethyllysine, a trimethylamine N-oxide precursor, provides near- and long-term prognostic value in patients presenting with acute coronary syndromes.三甲基赖氨酸是氧化三甲胺的前体，可为急性冠状动脉综合征患者提供近期和长期预后价值。
Eur Heart J. 2019 Aug 21;40(32):2700-2709. doi: 10.1093/eurheartj/ehz259.
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Benzoxaborole treatment perturbs S-adenosyl-L-methionine metabolism in Trypanosoma brucei.苯并恶硼烷处理扰乱了布鲁氏锥虫中的 S-腺苷-L-蛋氨酸代谢。
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4
Combined effect of ascorbic acid deficiency and underfeeding on the hepatic carnitine level in guinea-pigs.
Experientia. 1983 May 15;39(5):512-3. doi: 10.1007/BF01965181.
5
Carnitine biosynthesis. Hydroxylation of N6-trimethyl-lysine to 3-hydroxy-N6-trimethyl-lysine.肉碱生物合成。N6-三甲基赖氨酸羟基化为3-羟基-N6-三甲基赖氨酸。
Biochem J. 1980 May 15;188(2):529-34. doi: 10.1042/bj1880529.
6
N6-Trimethyl-lysine metabolism. Structural identification of the metabolite 3-hydroxy-N6-trimethyl-lysine.N6-三甲基赖氨酸代谢。代谢物3-羟基-N6-三甲基赖氨酸的结构鉴定。
Biochem J. 1980 May 15;188(2):521-7. doi: 10.1042/bj1880521.

本文引用的文献

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The availability of the acetyl derivatives of lysine for growth.赖氨酸乙酰衍生物对生长的可用性。
Biochem J. 1943 Oct;37(4):515-8. doi: 10.1042/bj0370515.
2
[STUDIES ON THE HYPOTENSIVE CONSTITUENTS OF MARINE ALGAE. II. SYNTHESIS OF LAMININE AND RELATED COMPOUNDS].
Yakugaku Zasshi. 1964 Dec;84:1180-2. doi: 10.1248/yakushi1947.84.12_1180.
3
ENZYMOLOGICAL DETERMINATION OF FREE CARNITINE CONCENTRATIONS IN RAT TISSUES.大鼠组织中游离肉碱浓度的酶学测定
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The separation and determination of cyclic imino acids.环状亚氨基酸的分离与测定。
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N6-Trimethyl-lysine metabolism. Structural identification of the metabolite 3-hydroxy-N6-trimethyl-lysine.N6-三甲基赖氨酸代谢。代谢物3-羟基-N6-三甲基赖氨酸的结构鉴定。
Biochem J. 1980 May 15;188(2):521-7. doi: 10.1042/bj1880521.
6
Gamma-butyrobetaine hydroxylase from Pseudomonas sp AK 1.来自假单胞菌属AK 1的γ-丁甜菜碱羟化酶
Biochemistry. 1970 Oct 27;9(22):4336-42. doi: 10.1021/bi00824a014.
7
Isolation and identification of N-G,N-G- and N-G,N'-G-dimethyl-arginine, N-epsilon-mono-, di-, and trimethyllysine, and glucosylgalactosyl- and galactosyl-delta-hydroxylysine from human urine.从人尿中分离并鉴定N-G、N-G-和N-G、N'-G-二甲基精氨酸、N-ε-单甲基、二甲基和三甲基赖氨酸，以及葡萄糖基半乳糖基-和半乳糖基-δ-羟基赖氨酸。
J Biol Chem. 1970 Nov 10;245(21):5751-8.
8
Protein methylation.蛋白质甲基化
Science. 1971 Oct 8;174(4005):114-9. doi: 10.1126/science.174.4005.114.
9
Role of lysine in carnitine biosynthesis in Neurospora crassa.赖氨酸在粗糙脉孢菌肉碱生物合成中的作用。
J Biol Chem. 1971 Jul 10;246(13):4373-5.
10
Biosynthesis of carnitine and 4-N-trimethylaminobutyrate from 6-N-trimethyl-lysine.由N6-三甲基赖氨酸合成肉碱和4-N-三甲基氨基丁酸
Biochem J. 1973 Dec;136(4):1083-90. doi: 10.1042/bj1361083.

N6-三甲基赖氨酸代谢。3-羟基-N6-三甲基赖氨酸与肉碱的生物合成。

N6-Trimethyl-lysine metabolism. 3-Hydroxy-N6-trimethyl-lysine and carnitine biosynthesis.

作者信息

Hoppel C L, Cox R A, Novak R F

出版信息

Biochem J. 1980 May 15;188(2):509-19. doi: 10.1042/bj1880509.

DOI:10.1042/bj1880509
PMID:6772168
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1161895/
Abstract

Rats injected with N6-[Me-3H]trimethyl-lysine excrete in the urine five radioactively labelled metabolites. Two of these identified metabolites are carnitine and 4-trimethylammoniobutyrate. A third metabolite, identified as 5-trimethylammoniopentanoate, is not an intermediate in the biosynthesis of carnitine; the fourth and major metabolite, N2-acetyl-N6-trimethyl-lysine, is not a precursor of carnitine. The remaining metabolite (3-hydroxy-N6-trimethyl-lysine) is converted into trimethylammoniobutyrate and carnitine by rat liver slices and into trimethylammoniobutyrate by rat kidney slices. In rat liver and kidney-slice experiments, radioactivity from DL-N6-trimethyl-[1-14C]lysine and DL-N6-trimethyl-[2-14C]lysine was incorporated into N2-acetyl-N6-trimethyl-lysine and 3-hydroxy-N6-trimethyl-lysine, but not into trimethylammoniobutyrate or carnitine. A procedure was devised to purify milligram quantities of 3-hydroxy-N6-trimethyl-lysine from the urine of rats injected chronically with N6-trimethyl-lysine (100 mg/kg body wt. per day). The structure of 3-hydroxy-N6-trimethyl-lysine was confirmed chemically and by nuclear-magnetic-resonance spectrometry [Novak, Swift & Hoppel (1980) Biochem. J. 188, 521--527]. The sequence for carnitine biosynthesis in liver is: N6-trimethyl-lysine leads to 3-hydryxy-N6-trimethyl-lysine leads to leads to 4-trimethylammoniobutyrate leads to carnitine.

摘要

注射了N6-[甲基-3H]三甲基赖氨酸的大鼠在尿液中排泄出五种放射性标记的代谢物。其中两种已鉴定的代谢物是肉碱和4-三甲基氨基丁酸。第三种代谢物被鉴定为5-三甲基氨基戊酸，它不是肉碱生物合成的中间体；第四种也是主要的代谢物N2-乙酰-N6-三甲基赖氨酸不是肉碱的前体。其余的代谢物（3-羟基-N6-三甲基赖氨酸）可被大鼠肝切片转化为三甲基氨基丁酸和肉碱，被大鼠肾切片转化为三甲基氨基丁酸。在大鼠肝和肾切片实验中，DL-N6-三甲基-[1-14C]赖氨酸和DL-N6-三甲基-[2-14C]赖氨酸的放射性被掺入N2-乙酰-N6-三甲基赖氨酸和3-羟基-N6-三甲基赖氨酸中，但未掺入三甲基氨基丁酸或肉碱中。设计了一种从长期注射N6-三甲基赖氨酸（每天100mg/kg体重）的大鼠尿液中纯化毫克量3-羟基-N6-三甲基赖氨酸的方法。通过化学方法和核磁共振光谱法确定了3-羟基-N6-三甲基赖氨酸的结构[诺瓦克、斯威夫特和霍佩尔（1980年）《生物化学杂志》188卷，521 - 527页]。肝脏中肉碱生物合成的顺序是：N6-三甲基赖氨酸生成3-羟基-N6-三甲基赖氨酸，进而生成4-三甲基氨基丁酸，最终生成肉碱。