β-内啡肽：27位酪氨酸被色氨酸取代可增强镇痛效力——2-硝基苯基亚磺酰衍生物的制备及性质
Beta-endorphin: replacement of tyrosine in position 27 by tryptophan increases analgesic potency--preparation and properties of the 2-nitrophenylsulfenyl derivative.
作者信息
Li C H, Yamashiro D, Nicolas P
出版信息
Proc Natl Acad Sci U S A. 1982 Feb;79(4):1042-4. doi: 10.1073/pnas.79.4.1042.
Abstract
An analog of human beta-endorphin with tryptophan in position 27 has been synthetized by the solid-phase method. Bioassay of the analog showed that it had almost 4 times the analgesic potency of the parent hormone but only 68% of the opiate receptor-binding activity. The peptide is the most potent analgesic among the known synthetic analogs of beta-endorphin. The 2-nitrophenylsulfenyl derivative of the analog has been prepared and shown to have a lower analgesic potency and a higher opiate receptor-binding activity than the parent compound.
摘要
已通过固相法合成了在第27位含有色氨酸的人β-内啡肽类似物。该类似物的生物测定表明，其镇痛效力几乎是母体激素的4倍，但阿片受体结合活性仅为母体激素的68%。该肽是已知的β-内啡肽合成类似物中镇痛效力最强的。已制备了该类似物的2-硝基苯硫基衍生物，结果表明其镇痛效力低于母体化合物，而阿片受体结合活性高于母体化合物。
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2
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3
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