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α-和β-黑素细胞刺激素的合成

Synthesis of alpha- and beta-melanocyte stimulating hormones.

作者信息

Yang Y C, Hruby V J, Heward C B, Hadley M E

出版信息

Int J Pept Protein Res. 1980 Feb;15(2):130-8.

PMID:7372404
Abstract

The solid phase synthesis of alpha-melanocyte stimulating hormone (alpha-MSH) using the benzhydrylamine resin and a number of recently described side chain protecting groups is given. The carboxamide terminal peptide was obtained directly by treatment of the peptide resin with liquid hydrogen fluoride at 0 degrees in the presence of carbonium ion scavengers. The solid phase synthesis of the C-terminal carboxylate hormone, porcine beta-melanocyte stimulating hormone (beta p-MSH), using a 1% cross-linked Merrifield resin and the same side chain protecting groups as in the alpha-MSH synthesis also is presented. Purification of both peptides was carried out by conventional chromatographic techniques. Both hormones were fully active and beta p-MSH was slightly more potent than previously reported in the literature.

摘要

本文给出了使用二苯甲基胺树脂和一些最近描述的侧链保护基团固相合成α-黑素细胞刺激素(α-MSH)的方法。在碳正离子清除剂存在下,于0℃用液态氟化氢处理肽树脂,直接得到酰胺末端肽。本文还介绍了使用1%交联的 Merrifield树脂和与α-MSH合成中相同的侧链保护基团固相合成C末端羧酸盐激素——猪β-黑素细胞刺激素(β p-MSH)的方法。两种肽均通过常规色谱技术进行纯化。两种激素均具有完全活性,且β p-MSH的效力略高于文献中先前报道的效力。

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Synthesis of alpha- and beta-melanocyte stimulating hormones.α-和β-黑素细胞刺激素的合成
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引用本文的文献

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Construction of a Tandem Repeat Peptide Sequence with Pepsin Cutting Sites to Produce Recombinant α-Melanocyte-Stimulating Hormone.构建具有胃蛋白酶切割位点的串联重复肽序列以产生重组α-促黑素细胞激素。
Molecules. 2021 Oct 14;26(20):6207. doi: 10.3390/molecules26206207.
2
4-Norleucine, 7-D-phenylalanine-alpha-melanocyte-stimulating hormone: a highly potent alpha-melanotropin with ultralong biological activity.4-去甲亮氨酸,7-D-苯丙氨酸-α-黑素细胞刺激素:一种具有超长生物活性的高效α-促黑素。
Proc Natl Acad Sci U S A. 1980 Oct;77(10):5754-8. doi: 10.1073/pnas.77.10.5754.
3
[half-Cys4,half-Cys10]-alpha-Melanocyte-stimulating hormone: a cyclic alpha-melanotropin exhibiting superagonist biological activity.
[半胱氨酸4,半胱氨酸10] -α-黑素细胞刺激素:一种具有超级激动剂生物活性的环状α-促黑素。
Proc Natl Acad Sci U S A. 1982 Mar;79(6):1751-5. doi: 10.1073/pnas.79.6.1751.