麦角固醇侧链生物合成的研究。
Studies on the biosynthesis of the ergosterol side chain.
作者信息
Akhtar M, Parvez M A, Hunt P F
出版信息
Biochem J. 1969 Jul;113(4):727-32. doi: 10.1042/bj1130727.
Abstract
- A convenient synthesis of 24-methylene[23,25-(3)H(3)]dihydrolanosterol is described. 2. A general anaerobic-aerobic method for the incorporation of sterols into whole yeast cells is also described and illustrated by experiments with (3)H-labelled lanosterol. 3. The method was used to convert labelled 24-methylene-dihydrolanosterol into ergosterol, in good yield, by Saccharomyces cerevisiae. 4. Degradation of the biosynthetic ergosterol provided confirmation of the conversion, which supports the proposed mechanism for the biosynthesis of the ergosterol side chain. 5. Mechanisms for the further conversion of the 24-methylene side chain into the ergosterol side chain are discussed and it was shown that a compound, [3alpha-(3)H(1)]-ergost-7-en-3beta-ol, with a fully saturated side chain, can also be efficiently incorporated into ergosterol. 6. This result was confirmed by a procedure involving formation of the 5,8-epidioxide and subsequently the 5,8-epidioxy-22,23-epoxide of the biosynthetic ergosterol.
摘要
- 描述了24-亚甲基[23,25-(3)H(3)]二氢羊毛甾醇的简便合成方法。2. 还描述了一种将甾醇掺入全酵母细胞的通用厌氧-需氧方法，并通过用(3)H标记的羊毛甾醇进行的实验进行了说明。3. 该方法用于通过酿酒酵母将标记的24-亚甲基二氢羊毛甾醇高产率地转化为麦角甾醇。4. 生物合成的麦角甾醇的降解证实了这种转化，这支持了所提出的麦角甾醇侧链生物合成机制。5. 讨论了24-亚甲基侧链进一步转化为麦角甾醇侧链的机制，结果表明，一种具有完全饱和侧链的化合物[3α-(3)H(1)]-麦角甾-7-烯-3β-醇也能有效地掺入麦角甾醇中。6. 通过涉及生物合成的麦角甾醇的5,8-环氧化物以及随后的5,8-环氧-22,23-环氧化物形成的程序证实了这一结果。
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引用本文的文献
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本文引用的文献
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The conversion of cholest-7-en-3beta-ol into cholesterol. General comments on the mechanism of the introduction of double bonds in enzymic reactions.胆甾-7-烯-3β-醇转变为胆固醇。关于酶反应中双键引入机制的一般评述。
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Net synthesis of sterols in resting cells of Saccharomyces cerevisiae.酿酒酵母静止细胞中甾醇的净合成
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The mechanism of introduction of alkyl groups at C-24 of sterols. II. The necessity of the delta-24 bond.甾醇C-24位引入烷基的机制。II. Δ24键的必要性。
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The mechanism of introduction of alkyl groups at C-24 of sterols. I. The precursor of the C2 group.甾醇C-24位引入烷基的机制。I. C2基团的前体。
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The transfer of hydrogen from C-24 to C-25 in ergosterol biosynthesis.麦角固醇生物合成过程中氢从C-24向C-25的转移。
Biochem J. 1967 Jun;103(3):616-22. doi: 10.1042/bj1030616.
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J Biol Chem. 1967 Jan 25;242(2):222-7.
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Nature. 1966 Jun 25;210(5043):1322-4. doi: 10.1038/2101322a0.
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Biochim Biophys Acta. 1968 Jul 1;152(4):742-8. doi: 10.1016/0005-2760(68)90120-3.
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