氚标记的异青霉素N、青霉素N和6-氨基青霉烷酸的合成。
Synthesis of tritium-labelled isopenicillin N, penicillin N and 6-aminopenicillanic acid.
作者信息
Usher J J, Loder B, Abraham E P
出版信息
Biochem J. 1975 Dec;151(3):729-39. doi: 10.1042/bj1510729.
Abstract
- Phenoxymethylpenicillin sulphoxide 4-methoxybenzyl ester was labelled with 3H in its 2-beta-methyl group. Its specific radioactivity was 362 mCi/mmol. 2. Removal of the side chain of this compound yielded the corresponding ester of 6-aminopenicillanic acid sulphoxide and coupling of the latter with the appropriate protected alpha-aminoadipic acid gave 4-methoxybenzyloxycarbonylisopenicillin N sulphoxide di-4-methoxybenzyl ester or the corresponding derivative of penicillin N. 3. Removal of the protective groups by hydrogenolysis and reduction of the sulphoxide group yielded 3H-labelled isopenicillin N or penicillin N. 4. 3H-labelled phenoxymethylpenicillin sulphoxide was obtained by hydrogenolysis from its 4-methoxybenzyl ester. Reduction of its sulphoxide group and subsequent removal of the side chain gave 3H-labelled 6-aminopenicillanic acid.
摘要
- 苯氧甲基青霉素亚砜4 - 甲氧基苄酯在其2-β-甲基上用³H标记。其比放射性为362 mCi/mmol。2. 去除该化合物的侧链得到6-氨基青霉烷酸亚砜的相应酯，后者与适当保护的α-氨基己二酸偶联得到4-甲氧基苄氧羰基异青霉素N亚砜二-4-甲氧基苄酯或青霉素N的相应衍生物。3. 通过氢解去除保护基团并还原亚砜基团得到³H标记的异青霉素N或青霉素N。4. 通过氢解从其4-甲氧基苄酯得到³H标记的苯氧甲基青霉素亚砜。还原其亚砜基团并随后去除侧链得到³H标记的6-氨基青霉烷酸。
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