SYNTHESIS OF RACEMIC [3-C-11]-LABELED ALANINE, 2-AMINOBUTYRIC ACID, NORVALINE, NORLEUCINE, LEUCINE AND PHENYLALANINE AND PREPARATION OF L-[3-C-11]ALANINE AND L-[3-C-11]PHENYLALANINE
SYNTHESIS OF RACEMIC [3-C-11]-LABELED ALANINE, 2-AMINOBUTYRIC ACID, NORVALINE, NORLEUCINE, LEUCINE AND PHENYLALANINE AND PREPARATION OF L-[3-C-11]ALANINE AND L-[3-C-11]PHENYLALANINE
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DOI：
10.1002/jlcr.2580240203
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发表时间：
1987-02-01
影响因子：
1.8
通讯作者：
LANGSTROM, B
中科院分区：
文献类型：
--
作者：
ANTONI, G;LANGSTROM, B
本文报道了外消旋[~（3- 11）C]-标记丙氨酸、2-氨基丁酸、正缬氨酸、正亮氨酸、亮氨酸和苯丙氨酸的合成。该反应是通过N-（二苯基亚甲基）-甘氨酸叔丁酯与适当的11 C-烷基碘的相转移烷基化反应进行的，然后酸水解，以10-55%的放射化学产率获得标记的氨基酸。L-[3- 11 C]-丙氨酸和L-[3- 11 C]-苯丙氨酸经固定化D-氨基酸氧化酶处理后，对映体过量均达到99%。在以120 mCi [11 C]二氧化碳开始的典型试验中，制备25 mCi [1- 11 C]苄基碘，并用于在50分钟内得到6 mCi DL-[3- 11 C]苯丙氨酸。在用D-氨基酸氧化酶处理后，在约100分钟的总合成时间后获得0.3mCi的L-[3- 11 C]苯丙氨酸。
The syntheses of racemic [3-11C]-labelled alanine, 2-aminobutyric acid, norvaline, norleucine, leucine and phenyl-alanine are reported. The reactions were performed by a phase-transfer alkylation reaction on N-(diphenylmethylene)-glycine tert-butyl ester with the appropriate 11C-alkyl iodides followed by acidic hydrolysis and the labelled amino acids were obtained in 10-55% radiochemical yield. L-[3-11C]-Alanine and L-[3-11C]phenylalanine were obtained in 99% enantiomeric excess after treatment of the corresponding racemic mixture by D-amino acid oxidase immobilized on glutaraldehyde-activated glass beads. In a typical run starting with 120 mCi [11C]carbon dioxide, 25 mCi [1-11C]benzyl iodide was prepared and used to give 6 mCi of DL-[3-11C]phenylalanine within 50 minutes. Following treatment with D-amino acid oxidase, 0.3 mCi of L-[3-11C]phenylalanine was obtained after a total synthesis time of about 100 minutes.