SYNTHESES AND BIOLOGICAL ACTIVITIES OF SOME CYCLOALKENEALANINES
SYNTHESES AND BIOLOGICAL ACTIVITIES OF SOME CYCLOALKENEALANINES
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DOI：
10.1021/jm00308a016
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发表时间：
1968-01-01
影响因子：
7.3
通讯作者：
SHIVE, W
中科院分区：
文献类型：
--
作者：
PORTER, TH;GIPSON, RM;SHIVE, W
合成了DL-3-环戊烯-1-丙氨酸、DL-2-环戊烯-1-丙氨酸、DL-2-环己烯-1-丙氨酸和DL-1-环庚烯-1-丙氨酸等脂环族氨基酸，并测定了它们对几种微生物生长的影响。DL-3-环戊烯-L-丙氨酸对大肠杆菌和乳酸菌植物乳杆菌8014的生长有抑制作用; coli 10856中的亮氨酸仅在少量补充蛋氨酸的情况下以竞争性方式逆转，其方式表明亮氨酸类似物抑制亮氨酸的利用和蛋氨酸的生物合成。DL-2-环己烯-l-丙氨酸和DL-2-环戊烯-l-丙氨酸抑制葡聚糖明串珠菌8086的生长，并且这两种类似物的毒性通过增加亮氨酸浓度以竞争性方式逆转超过10-20倍范围。DL-1-环庚烯-L-丙氨酸仅在很高的水平下才能抑制葡聚糖明串珠菌8086的生长，而苯丙氨酸不能逆转其毒性。例如，已发现1-环戊烯-L-丙氨酸和1-环己烯-L-丙氨酸是苯丙氨酸的竞争性拮抗剂，而相应的饱和衍生物环戊基丙氨酸和环己烷基丙氨酸在所研究的微生物中仅具有轻微的亮氨酸拮抗活性，而后者没有明显的抗代谢活性。
The alicyclic amino acids, DL-3-cyclopentene-l-alanine, DL-2-cyclopentene-l-alanine, DL-2-cyclohexene-lalanine, and DL-l-cycloheptene-l-alanine were synthesized, and their effects upon thegrowth of several micro-organisms were determined. DL-3-Cyclopentene-l-alanine inhibits the growth of three Escherichia coli strains and the lactic acid bacteria, Lactobacillus plantarum 8014; the growth inhibition of E. coli 10856is reversed in a competitivelike manner by leucine only in the presence of a small supplement of methionine in a manner suggest-ing that the analog inhibits utilization of leucine and the biosynthesis of methionine. DL-2-Cyclohexene-lalanine and DL-2-cyclopentene-l-alamne inhibit the growth of Leuconostoc dextranicum 8086, and the toxicities of both analogs were reversed in a competitivelike manner over a 10-20-fold range by increasing concentrations of leucine. DL-l-Cycloheptene-l-alanine prevented the growth of Leuconostoc dextranicum 8086 only at very high levels; no reversal of toxicity could be demonstrated with phenylalanine.Several alicylic amino acids have been reported to have rather specific antimetabolite activity, and the structural relationships between the natural metabolites and the active analogs have demonstrated the importance of steric factors in the biological activity of these compounds. For example, 1-cyclopentene-lalanine and l-cyclohexene-l-alanine have been found to be competitive antagonists of phenylalanine in con-trast to the corresponding saturatedderivatives, cyclopentanealanine and cyclohexanealanine, the first of which has slight activity only as a leucine antagonist and the second of which has no demonstrable anti-metabolite activity in the microorganisms studied.