ARSENIC COMPOUNDS FROM THE KIDNEY OF THE GIANT CLAM TRIDACNA-MAXIMA - ISOLATION AND IDENTIFICATION OF AN ARSENIC-CONTAINING NUCLEOSIDE
ARSENIC COMPOUNDS FROM THE KIDNEY OF THE GIANT CLAM TRIDACNA-MAXIMA - ISOLATION AND IDENTIFICATION OF AN ARSENIC-CONTAINING NUCLEOSIDE
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DOI：
10.1039/p19920001349
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发表时间：
1992-06-07
期刊：
影响因子：
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通讯作者：
STICK, RV
中科院分区：
文献类型：
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作者：
FRANCESCONI, KA;EDMONDS, JS;STICK, RV
大砗磲的肾脏含有藻砷化合物，可能是由于蛤与单细胞藻类（虫黄藻）的共生关系。三爪鼠肾的提取得到三种新的砷化合物，N-（5'-脱氧-5'-二甲基larsinyl - β -d -核糖基羰基）甘氨酸5，(2S)-3-（5'-脱氧-5'-二甲基larsinyl - β -d -核糖基）-2-羟基propanoic acid 4a和(2R)-3-（5'-脱氧-5'-二甲基larsinyl - β -d -核糖基）-2-羟基propanoic acid 4b，以及先前报道的四种二甲基larsinyl核苷。这3个新化合物的结构主要由核磁共振数据确定，化合物4a和4b的结构经合成证实。第二批三叶鼠肾的提取，除了在第一次提取中发现的化合物外，还得到(2S)-3-[（5'-脱氧-5'-三甲基larsono - β -d -核糖氧基）-2-羟丙基]硫酸盐18和两种新的化合物：含砷核苷，9-(5'-脱氧-5'-二甲基larsinyl)- 9h -腺苷16和N-[4-（二甲基larsinyl）丁醇]牛磺酸21。报道了化合物16和21的合成。作为藻类代谢的结果，核苷16在砗齿纲中的存在，支持了藻类含砷核苷生物发生的途径，包括s -腺苷蛋氨酸的甲基化和腺苷化。化合物21的生物遗传途径涉及s -腺苷蛋氨酸的3-氨基-3-羧基丙基部分的捐赠。Tridacna中化合物16和21的存在可能代表了s -腺苷蛋氨酸在一个生物体内将其所有三个烷基都捐赠给单一受体（砷）的第一个例子。
The kidney of the giant clam Tridacna maxima contains algal arsenic compounds, probably as a consequence of the clam's symbiotic relationship with unicellular algae (zooxanthallae). Extraction of Tridacna kidneys yielded three novel arsenic compounds, N-(5'-deoxy-5'-dimethylarsinoyl-beta-D-ribosyloxycarbonyl)glycine 5, (2S)-3-(5'-deoxy-5'-dimethylarsinoyl-beta-D-ribosyloxy)-2-hydroxypropanoic acid 4a, and (2R)-3-(5'-deoxy-5'-dimethylarsinoyl-beta-D-ribosyloxy)-2-hydroxypropanoic acid 4b, in addition to four previously reported dimethylarsinoylribosides. The structures of the three new compounds were assigned chiefly from NMR data, and those for compounds 4a and 4b were confirmed by synthesis. Extraction of a second batch of Tridacna kidneys gave, in addition to compounds identified in the first extraction, (2S)-3-[(5'-deoxy-5'-trimethylarsonio-beta-D-ribosyloxy)-2-hydroxypropyl]sulfate 18 and two novel compounds: an arsenic-containing nucleoside, 9-(5'-deoxy-5'-dimethylarsinoyl)-9H-adenosine 16 and N-[4-(dimethylarsinoyl)butanoyl]taurine 21. Syntheses of compounds 16 and 21 are reported. The presence of the nucleoside 16 in Tridacna, as a consequence of algal metabolism, supports a proposed pathway for the biogenesis of arsenic-containing ribosides by algae involving methylation and adenosylation by S-adenosylmethionine. A biogenetic pathway for compound 21 involving donation of the 3-amino-3-carboxypropyl moiety of S-adenosylmethionine is also proposed. The presence of both compounds 16 and 21 in Tridacna may represent the first example of donation, by S-adenosylmethionine, of all three of its alkyl groups to a single acceptor (arsenic) within one organism.