REACTIONS OF ALKYLCOBALAMINS

REACTIONS OF ALKYLCOBALAMINS
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DOI:
10.1039/jr9640003186
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发表时间:
1964-01-01
期刊:
JOURNAL OF THE CHEMICAL SOCIETY
影响因子:
--
通讯作者:
RODRIGO, R
RODRIGO, R
中科院分区:
其他
文献类型:
--
作者:
DOLPHIN, D;JOHNSON, AW;RODRIGO, R

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自从维生素B结构确定以来,(5 '-脱氧腺苷钴胺素)(I; R= 5 '-脱氧腺苷)通过X射线晶体学,a从维生素B12 b部分合成辅酶(羟钴胺)(I; R= H,O)已经被开发293,其涉及还原成所谓的维生素B12,现在认为是氢化钴2-5(维生素B12)(I; R= H)和与2 ',3'-0-异亚丙基-5 '-甲苯磺酰腺苷反应,最终水解除去异亚丙基。在该反应中使用简单的烷基卤使得多种烷基钴胺素(I; R=烷基)可用于研究其化学和生物反应。烷基钴胺素的替代部分合成包括将乙炔或活化烯烃加成到羟钴胺上,或使烷基卤化物与羟钴胺与硫醇反应形成的产物反应,6这一反应可能与辅酶的生化合成有关。
SINCE the determination of the structure of the vitamin B,, coenzyme (5’-deoxyadenosylcobalamin)(I; R= 5’-deoxyadenosyl) by X-ray crystallography, la partial synthesis of the coenzyme from vitamin B12b (hydroxocobalamin)(I; R= H, O) has been developed 293 which involves reduction to the so-called vitamin B12s, now thought to be a cobalt hydride 2-5(hydridocobalamin)(I; R= H) and reaction with 2 ‘, 3’-0-isopropylidene-5’-tosyladenosine with a final hydrolytic removal of the isopropylidene group. The use of simple alkyl halides in this reaction has made a wide variety of alkylcobalamins (I; R= alkyl) available for the study of their chemical and biological reactions. Alternative partial syntheses of alkylcobalamins involve the addition of acetylenes or activated olefines to hydridocobalamin or the reaction of alkyl halides with the products formed from the reaction of hydroxocobalamin with thiols, 6 a reaction which is probably related to the biochemical synthesis of the coenzyme.’