Syntheses and biological activities of parallel and antiparallel homo and hetero bis-cystine dimers of oxytocin and deamino-oxytocin.

Peptide research Pub Date : 1996-05-01
L Chen, H Bauerová, J Slaninová, G Barany
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Abstract

New methods have been developed for the synthesis of disulfide-bridged homo and hetero peptide dimers (both parallel and antiparallel), as exemplified in the oxytocin and deamino-oxytocin families. The linear sequences were assembled by 9-fluorenyl-methyloxycarbonyl (Fmoc) solid-phase synthesis techniques, with orthogonal protection for the two beta-thiols by appropriate combinations of S-[(N'-methyl-N'-phenylcarbamoyl)sulfernyl] (Snm), S-acetamido-methyl (Acm) and S-2, 4, 6-trimethoxybenzyl (Tmob) groups. Two octapeptide-resins gave rise to four different nonapeptide amides, which were brought together in defined ways to provide access to four of the six possible dimeric products. For each dimer, the first disulfide bond was formed in solution by a directed method, and then the second disulfide bond was formed, without purification of the intermediates, by iodine oxidation. Final isolated yields of the desired pure dimers were in the 20% to 40% range. Biological activities ranged from 0.2% to 6% that of oxytocin, depending on the assay, and were in some cases considerably protracted. These data are consistent with the hypothesis that dimers revert slowly to monomers under the testing conditions.

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后叶催产素和去氨基后叶催产素平行和反平行同异双胱氨酸二聚体的合成及其生物学活性。
新方法已经开发用于合成二硫桥接的同肽和异肽二聚体(平行和反平行),例如在催产素和去氨基-催产素家族。采用9-芴基-甲基氧羰基(Fmoc)固相合成技术组装线性序列,并通过S-[(N'-甲基-N'-苯基氨基甲酰基)磺酰基](Snm)、S-乙酰氨基甲基(Acm)和S- 2,4,6 -三甲氧基苯基(Tmob)基团的适当组合对两个β -硫醇进行正交保护。两种八肽树脂产生了四种不同的非肽酰胺,它们以确定的方式聚集在一起,提供了六种可能的二聚体产物中的四种。对于每个二聚体,第一个二硫键是在溶液中通过定向方法形成的,然后第二个二硫键是在没有纯化中间体的情况下通过碘氧化形成的。所期望的纯二聚体的最终分离收率在20%至40%的范围内。生物活性范围从0.2%到6%的催产素,取决于化验,在某些情况下相当长的时间。这些数据与二聚体在测试条件下缓慢还原为单体的假设是一致的。
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