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含有单糖或单糖衍生物的促吞噬素和瑞吉因衍生物的合成及生物活性

Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives.

作者信息

Rocchi R, Biondi L, Cavaggion F, Filira F, Gobbo M, Dagan S, Fridkin M

出版信息

Int J Pept Protein Res. 1987 Feb;29(2):262-75. doi: 10.1111/j.1399-3011.1987.tb02253.x.

DOI:10.1111/j.1399-3011.1987.tb02253.x
PMID:3570666
Abstract

Synthesis of some modified rigins is described in which either D-gluconic acid or 2-amino-2-deoxy-beta-D-glucopyranose have been linked to the parent molecule through amide bonds involving the alpha-amino function, alpha-carboxyl function or the gamma-amide function of glutamine in position 2. Glu2-rigin and D-gluconyl-Glu2-rigin have also been synthesized. Binding and phagocytosis assays have been carried out on the rigin derivatives and on some glycosylated tuftsin derivatives as well. Of all the tested peptides only rigin enhanced the phagocytic capacity of mouse peritoneal macrophages to the same extent as tuftsin. The peptides H-Thr-Lys-Pro-Arg-NH-Glc and N alpha-gluconyl-Gly-Glu-Pro-Arg-OH slightly enhanced phagocytosis. H-Thr[(alpha + beta)-O-glucosyl]-Lys-Pro-Arg-OH was found to displace 3H-tuftsin even better than tuftsin but lacked the ability to stimulate phagocytosis.

摘要

描述了一些修饰的瑞吉因(rigin)的合成,其中D-葡萄糖酸或2-氨基-2-脱氧-β-D-吡喃葡萄糖通过涉及2位谷氨酰胺的α-氨基功能、α-羧基功能或γ-酰胺功能的酰胺键与母体分子相连。还合成了Glu2-瑞吉因和D-葡萄糖酰基-Glu2-瑞吉因。对瑞吉因衍生物以及一些糖基化的促吞噬素(tuftsin)衍生物进行了结合和吞噬试验。在所有测试的肽中,只有瑞吉因能像促吞噬素一样增强小鼠腹腔巨噬细胞的吞噬能力。肽H-Thr-Lys-Pro-Arg-NH-Glc和Nα-葡萄糖酰基-Gly-Glu-Pro-Arg-OH略微增强了吞噬作用。发现H-Thr[(α+β)-O-葡萄糖基]-Lys-Pro-Arg-OH比促吞噬素更能取代3H-促吞噬素,但缺乏刺激吞噬作用的能力。

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Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives.含有单糖或单糖衍生物的促吞噬素和瑞吉因衍生物的合成及生物活性
Int J Pept Protein Res. 1987 Feb;29(2):262-75. doi: 10.1111/j.1399-3011.1987.tb02253.x.
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Synthesis of modified tuftsins containing monosaccharides or monosaccharide derivatives.
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