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83936-23-6,五肽β-Casomorphin (1-5), amide, bovine,H2N-Tyr-DAla-Phe-Pro-Met-NH2,H2N-Y-DAla-FPM-NH2,杭州专肽生物的产品

β-Casomorphin (1-5), amide, bovine

牛 β-Casomorphin 的多肽片段。

编号:200643

CAS号:83936-23-6

单字母:H2N-YaFPM-NH2

纠错
  • 编号:200643
    中文名称:β-Casomorphin (1-5), amide, bovine
    英文名:β-Casomorphin (1-5), amide, bovine
    CAS号:83936-23-6
    单字母:H2N-YaFPM-NH2
    三字母:H2N

    N端氨基

    -Tyr

    酪氨酸

    -DAla

    D型丙氨酸

    -Phe

    苯丙氨酸

    -Pro

    脯氨酸

    -Met

    甲硫氨酸

    -NH2

    C端酰胺化

    氨基酸个数:5
    分子式:C31H42N6O6S1
    平均分子量:626.77
    精确分子量:626.29
    等电点(PI):-
    pH=7.0时的净电荷数:1.97
    平均亲水性:-1.925
    疏水性值:0.8
    消光系数:1490
    来源:人工化学合成,仅限科学研究使用,不得用于人体。
    储存条件:负80℃至负20℃
    标签:D型氨基酸肽    酪啡肽(β-Casomorphin)   

  • β-Casomorphin (1-5), amide, bovine 是牛 β-Casomorphin 的多肽片段。
    β-Casomorphin (1-5), amide, bovine is a peptide of bovine β-Casomorphin.

    很多蛋白在细胞中非常容易被降解,或被标记,进而被选择性地破坏。但含有部分D型氨基酸的多肽则显示了很强的抵抗蛋白酶降解能力。

    酪啡肽(β-Casomorphin)的定义

    β-酪啡肽是由β-酪蛋白消化产生的肽,长度为 4-11 个氨基酸。  它们表现出阿片类药物或吗啡样功能。

    酪啡肽(β-Casomorphin)的发现

    β-酪啡肽首先从豚鼠回肠的酪蛋白消化物中纯化,基于其显示阿片类活性的能力。 

    酪啡肽(β-Casomorphin)的分类

    ß-酪啡肽是阿片肽。已鉴定出几种天然存在的β-酪啡肽 (BCM):牛 BCM-4、牛 BCM-5、牛 BCM-6、牛 BCM-7、牛 BCM-8、牛 BCM-11、人 BCM-7、人 BCM-8 。  已经合成了几种类似物,它们是天然存在的 BCM 的结构修饰变体。

    酪啡肽(β-Casomorphin)的结构特点

    BCM 的长度为 4-11 个氨基酸。天然存在的 BCM 的序列如下1所示:

    牛 BCM-4        Tyr-Pro-Phe-Pro

    牛 BCM-5        Tyr-Pro-Phe-Pro-Gly

    牛 BCM-6        Tyr-Pro-Phe-Pro-Gly-Pro

    牛 BCM-7        Tyr-Pro-Phe-Pro-Gly-Pro-Ile

    牛 BCM-8        Tyr-Pro-Phe-Pro-Gly-Pro-Ile-Pro

    牛 BCM-11       Tyr-Pro-Phe-Pro-Gly-Pro-Ile-Pro-Asn-Ser-Leu

    人 BCM-7        Tyr-Pro-Phe-Val-Glu-Pro-Ile

    人 BCM-8        Tyr-Pro-Phe-Val-Glu-Pro-Ile-Pro

    BCM类似物的一些序列如下所示:

    H-Tyr-Pro-Phe-Pro-Gly-EtDA-Gly-II

    H-Tyr-Pro-Phe-Pro-Gly-EtDA-Gly-Gly-II

    H-Tyr-Pro-Phe-Pro-Gly-EtDA-Gly-Gly-CO-CH3

    H-Tyr-Pro-Phe-Pro-Gly-EtDA-Gly-Gly-CO-CH2-CH2-COOH

    酪啡肽(β-Casomorphin)的作用方式

    关于 BCM 功能的确切机制目前还没有太多研究。众所周知,它们通过与细胞膜上的阿片受体结合来发挥阿片功能。  最近的研究表明,BCM-7 是大脑中血管紧张素受体的高亲和力配体。

    酪啡肽(β-Casomorphin)的功能

    BCM 对胃肠道产生影响。  例如,它们通过刺激胰岛素和生长抑素的分泌来影响餐后代谢,并调节肠道中氨基酸的转移5。  影响缺氧,因为已经表明,当给怀孕大鼠施用 BCM7 时,可以诱导其从缺氧状态中恢复。  BCM-5 和类似物参与大鼠旋转行为的产生。  BCM-8 参与哺乳期间母亲和孩子之间的相互作用。  最后,BCM 与多种疾病有关,包括 SIDS 和儿童自闭症。

    酪啡肽(β-Casomorphin)的相关文献

    1、Kamiñski S, Cieoeliñska A, Kostyra E (2007). Polymorphism of bovine beta-casein and its potential effect on human health. J Appl Genet, 48(3), 189–198.

    2、Ramabadran K, Bansinath M (1989). Pharmacology of beta-casomorphins, opioid peptides derived from milk protein. Asia Pac J Pharmacol, 4, 45–58.

    3、Sobirov MM, Khalikov ShKh, Saidov SS, Kodirov MZ, Zaitsev SV, Chichenkov ON, Varfolomeev SD (1994). Synthesis and biological activity of new analogs of beta-casomorphine-5. Bioorg Khim., 20(7), 740-50.

    4、Book: Handbook of Biologically Active Peptides by Abba J. Kastin.

    5、Zoghbi S, Trompette A, Claustre J, Homsi ME, Garzo´n J, Jourdan G, Scoazec JY and Plaisancie P (2006). Casomorphin-7 regulates the secretion and expression of gastrointestinal mucins through a opioid pathway. Am J Physiol Gastrointest Liver Physiol 290, G1105–G1113.

    6、Marschitz HM, Terenius L, Grehn L, Ungerstedt U (1989). Rotational behaviour produced by intranigral injections of bovine and human beta-casomorphins in rats. Psychopharmacology (Berl), 99(3), 357-61.

    7、Ivano DN, Richard JF, Hannu JTK, Yves LR, Chris TL, Inga T, Daniel T, Renger W, (2009). Review of the potential health impact of ß-casomorphins and related peptides. EFSA Scientific Report, 231, 1-107.

     

    Definition

    Casomorphins are peptides resulting from the digestion of beta-Casein and vary from 4-11 amino acids in length1.  They exhibit opioid or morphine-like functions1.

    Discovery

    Casomorphins were first purified from casein digest of guinea pig ileum based on their ability to show opioid activity2. 

    Classification

    Casomorphins are opioid peptides1. The most commonly studied peptides are ß-Casomorphins (BCM) which are several in number: Bovine BCM-4, Bovine BCM-5, Bovine BCM-6, Bovine BCM-7, Bovine BCM-8, Bovine BCM-11, Human BCM-7, Human BCM-81. 

    Structural Characteristics

    BCMs are 4-11 amino acids in length. The sequences of naturally occurring BCMs are given below1:

    Bovine BCM-4        Tyr-Pro-Phe-Pro,

    Bovine BCM-5        Tyr-Pro-Phe-Pro-Gly

    Bovine BCM-6        Tyr-Pro-Phe-Pro-Gly-Pro

    Bovine BCM-7        Tyr-Pro-Phe-Pro-Gly-Pro-Ile

    Bovine BCM-8        Tyr-Pro-Phe-Pro-Gly-Pro-Ile-Pro

    Bovine BCM-11      Tyr-Pro-Phe-Pro-Gly-Pro-Ile-Pro-Asn-Ser-Leu

    Human BCM-7        Tyr-Pro-Phe-Val-Glu-Pro-Ile

    Human BCM-8        Tyr-Pro-Phe-Val-Glu-Pro-Ile-Pro

    Mode of action

    The exact mechanism of BCM function is not known. They exert their opioid functions by binding to opioid receptors on cell membranes4.  Recent studies have shown that BCM-7 is an high affinity ligand for angiotensin receptor in the brain4.

    Functions

    BCMs produce effects in the gastrointestinal tract.  For instance they influence post prandial metabolism by stimulating the secretion of insulin and somatostatin and modulate transfer of amino acids in the intestine5.  The affect hypoxia as it has been shown that BCM7 when administered to pregnant rats induces their recovery from hypoxic condition4.  BCM-5 and analogs are involved in producing rotational behavior in rats6.  BCM-8 is involved in interplay between mother and child during lactation7.  Finally, BCMs have been implicated in several diseases including SIDS and childhood autism1.

    References

    1.     Kamiñski S, Cieoeliñska A, Kostyra E (2007). Polymorphism of bovine beta-casein and its potential effect on human health. J Appl Genet, 48(3),189–198.

    2.     Ramabadran K, Bansinath M (1989). Pharmacology of beta-casomorphins, opioid peptides derived from milk protein. Asia Pac J Pharmacol, 4, 45–58.

    3.     Sobirov MM, Khalikov ShKh, Saidov SS, Kodirov MZ, Zaitsev SV, Chichenkov ON, Varfolomeev SD (1994). Synthesis and biological activity of new analogs of beta-casomorphine-5. Bioorg Khim., 20(7), 740-50.

    4.     Book: Handbook of Biologically Active Peptides by Abba J. Kastin.

    5.     Zoghbi S, Trompette A, Claustre J, Homsi ME, Garzo´n J, Jourdan G, Scoazec JY and Plaisancie P (2006). Casomorphin-7 regulates the secretion and expression of gastrointestinal mucins through a opioid pathway. Am J Physiol Gastrointest Liver Physiol,  290, G1105–G1113.

    6.     Marschitz HM, Terenius L, Grehn L, Ungerstedt U (1989). Rotational behaviour produced by intranigral injections of bovine and human beta-casomorphins in rats. Psychopharmacology (Berl)., 99(3), 357-61.

    7.     Ivano DN, Richard JF, Hannu JTK, Yves LR, Chris TL, Inga T, Daniel T, Renger W, (2009). Review of the potential health impact of ß-casomorphins and related peptides.  EFSA Scientific Report, 231, 1-107.

     

  • 多肽H2N-Tyr-DAla-Phe-Pro-Met-NH2的合成步骤:

    1、合成MBHA树脂:取若干克的MBHA树脂(如初始取代度为0.5mmol/g)和1倍树脂摩尔量的Fmoc-Linker-OH加入到反应器中,加入DMF,搅拌使氨基酸完全溶解。再加入树脂2倍量的DIEPA,搅拌混合均匀。再加入树脂0.95倍量的HBTU,搅拌混合均匀。反应3-4小时后,用DMF洗涤3次。用2倍树脂体积的10%乙酸酐/DMF 进行封端30分钟。然后再用DMF洗涤3次,甲醇洗涤2次,DCM洗涤2次,再用甲醇洗涤2次。真空干燥12小时以上,得到干燥的树脂{Fmoc-Linker-MHBA Resin},测定取代度。这里测得取代度为 0.3mmol/g。结构如下图:

    2、脱Fmoc:取1.87g的上述树脂,用DCM或DMF溶胀20分钟。用DMF洗涤2遍。加3倍树脂体积的20%Pip/DMF溶液,鼓氮气30分钟,然后2倍树脂体积的DMF 洗涤5次。得到 H2N-Linker-MBHA Resin 。(此步骤脱除Fmoc基团,茚三酮检测为蓝色,Pip为哌啶)。结构图如下:

    3、缩合:取1.68mmol Fmoc-Met-OH 氨基酸,加入到上述树脂里,加适当DMF溶解氨基酸,再依次加入3.37mmol DIPEA,1.6mmol HBTU。反应30分钟后,取小样洗涤,茚三酮检测为无色。用2倍树脂体积的DMF 洗涤3次树脂。(洗涤树脂,去掉残留溶剂,为下一步反应做准备)。得到Fmoc-Met-Linker-MBHA Resin。氨基酸:DIPEA:HBTU:树脂=3:6:2.85:1(摩尔比)。结构图如下:

    4、依次循环步骤二、步骤三,依次得到

    H2N-Met-Linker-MBHA Resin

    Fmoc-Pro-Met-Linker-MBHA Resin

    H2N-Pro-Met-Linker-MBHA Resin

    Fmoc-Phe-Pro-Met-Linker-MBHA Resin

    H2N-Phe-Pro-Met-Linker-MBHA Resin

    Fmoc-DAla-Phe-Pro-Met-Linker-MBHA Resin

    H2N-DAla-Phe-Pro-Met-Linker-MBHA Resin

    Fmoc-Tyr(tBu)-DAla-Phe-Pro-Met-Linker-MBHA Resin

    以上中间结构,均可在专肽生物多肽计算器-多肽结构计算器中,一键画出。

    最后再经过步骤二得到 H2N-Tyr(tBu)-DAla-Phe-Pro-Met-Linker-MBHA Resin,结构如下:

    5、切割:6倍树脂体积的切割液(或每1g树脂加8ml左右的切割液),摇床摇晃 2小时,过滤掉树脂,用冰无水乙醚沉淀滤液,并用冰无水乙醚洗涤沉淀物3次,最后将沉淀物放真空干燥釜中,常温干燥24小试,得到粗品H2N-Tyr-DAla-Phe-Pro-Met-NH2。结构图见产品结构图。

    切割液选择:1)TFA:H2O=95%:5%

    2)TFA:H2O:TIS=95%:2.5%:2.5%

    3)三氟乙酸:茴香硫醚:1,2-乙二硫醇:苯酚:水=87.5%:5%:2.5%:2.5%:2.5%

    (前两种适合没有容易氧化的氨基酸,例如Trp、Cys、Met。第三种适合几乎所有的序列。)

    6、纯化冻干:使用液相色谱纯化,收集目标峰液体,进行冻干,获得蓬松的粉末状固体多肽。不过这时要取小样复测下纯度 是否目标纯度。

    7、最后总结:

    杭州专肽生物技术有限公司(ALLPEPTIDE https://www.allpeptide.com)主营定制多肽合成业务,提供各类长肽,短肽,环肽,提供各类修饰肽,如:荧光标记修饰(CY3、CY5、CY5.5、CY7、FAM、FITC、Rhodamine B、TAMRA等),功能基团修饰肽(叠氮、炔基、DBCO、DOTA、NOTA等),同位素标记肽(N15、C13),订书肽(Stapled Peptide),脂肪酸修饰肽(Pal、Myr、Ste),磷酸化修饰肽(P-Ser、P-Thr、P-Tyr),环肽(酰胺键环肽、一对或者多对二硫键环),生物素标记肽,PEG修饰肽,甲基化修饰肽

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