Bahyrycz Agata, Matsubayashi Yoshikatsu, Ogawa Mari, Sakagami Youji, Konopińska Danuta
Faculty of Chemistry, University of Wrocław, 50-383 Wrocław, ul. F. Joliot-Curie 14, Poland.
J Pept Sci. 2005 Sep;11(9):589-92. doi: 10.1002/psc.653.
Phytosulfokine-alpha (PSK-alpha), a sulfated growth factor of structure H-Tyr(SO3H)-Ile-Tyr(SO3H)-Thr-Gln-OH universally found in both monocotyledons and dicotyledons, strongly promotes proliferation of plant cells in culture. In studies on the structure/activity relationship of PSK-alpha the synthesis was performed of a series of a further 23 analogues modified in position 1, 3 or 4 as well as simultaneously in positions 1 and 3 of the peptide chain. Peptides were synthesized by the solid phase method according to the Fmoc procedure on a Wang-resin. Free peptides were released from the resin by 95% TFA in the presence of EDT. All peptides were tested by competitive binding assay to the carrot membrane using 3H-labelled PSK-alpha according to the test of Matsubayashi et al. Among these peptide analogues, [H-Phe(4-Cl)1]-PSK-alpha (IV), [H-Phe(4-I)1]-PSK-alpha (VII), and [Phe(4-Cl)3]-PSK-alpha (XI) retained 30% PSK-alpha activity. Analogue [Tyr(PO3H2)3]-PSK-alpha (IX) showed 10% of PSK-alpha activity.
植物磺肽素-α（PSK-α）是一种结构为H-Tyr(SO3H)-Ile-Tyr(SO3H)-Thr-Gln-OH的硫酸化生长因子，在单子叶植物和双子叶植物中普遍存在，能强烈促进培养中的植物细胞增殖。在对PSK-α结构/活性关系的研究中，合成了另外23种类似物，这些类似物在肽链的第1、3或4位以及同时在第1和3位进行了修饰。肽通过固相法按照Fmoc程序在Wang树脂上合成。游离肽在EDT存在下用95%的三氟乙酸从树脂上释放出来。根据Matsubayashi等人的试验，使用3H标记的PSK-α通过与胡萝卜膜的竞争性结合试验对所有肽进行了测试。在这些肽类似物中，[H-Phe(4-Cl)1]-PSK-α（IV）、[H-Phe(4-I)1]-PSK-α（VII）和[Phe(4-Cl)3]-PSK-α（XI）保留了30%的PSK-α活性。类似物[Tyr(PO3H2)3]-PSK-α（IX）显示出10%的PSK-α活性。
