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93755-85-2,胃泌素释放肽,H2N-Val-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr-Val-Leu-Thr-Lys-Met-Tyr-Pro-Arg-Gly-Asn-His-Trp-Ala-Val-Gly-His-Leu-Met-NH2,H2N-VPLPAGGGTVLTKMYPRGNHWAVGHLM-NH2,杭州专肽生物的产品

胃泌素释放肽

Gastrin-Releasing Peptide, human (GRP) 属于Bombesin样肽家族,不是经典的下丘脑-垂体调节激素, 因为胃泌素释放肽 (GRP) 对垂体激素释放的调解中只起微弱作用。

编号:148861

CAS号:93755-85-2

单字母:H2N-VPLPAGGGTVLTKMYPRGNHWAVGHLM-NH2

纠错
  • 编号:148861
    中文名称:胃泌素释放肽
    英文名:GastrinReleasing Peptide , human
    CAS号:93755-85-2
    单字母:H2N-VPLPAGGGTVLTKMYPRGNHWAVGHLM-NH2
    三字母:H2N

    N端氨基

    -Val

    缬氨酸

    -Pro

    脯氨酸

    -Leu

    亮氨酸

    -Pro

    脯氨酸

    -Ala

    丙氨酸

    -Gly

    甘氨酸

    -Gly

    甘氨酸

    -Gly

    甘氨酸

    -Thr

    苏氨酸

    -Val

    缬氨酸

    -Leu

    亮氨酸

    -Thr

    苏氨酸

    -Lys

    赖氨酸

    -Met

    甲硫氨酸

    -Tyr

    酪氨酸

    -Pro

    脯氨酸

    -Arg

    精氨酸

    -Gly

    甘氨酸

    -Asn

    天冬酰胺

    -His

    组氨酸

    -Trp

    色氨酸

    -Ala

    丙氨酸

    -Val

    缬氨酸

    -Gly

    甘氨酸

    -His

    组氨酸

    -Leu

    亮氨酸

    -Met

    甲硫氨酸

    -NH2

    C端酰胺化

    氨基酸个数:27
    分子式:C130H204N38O31S2
    平均分子量:2859.38
    精确分子量:2857.5
    等电点(PI):-
    pH=7.0时的净电荷数:4.45
    平均亲水性:-0.83684210526316
    疏水性值:0.11
    外观与性状:白色粉末状固体
    消光系数:6990
    来源:人工化学合成,仅限科学研究使用,不得用于人体。
    纯度:95%、98%
    盐体系:可选TFA、HAc、HCl或其它
    生成周期:2-3周
    储存条件:负80℃至负20℃
    标签:胃泌素   

  • Gastrin-Releasing Peptide, human (GRP) 属于Bombesin样肽家族,不是经典的下丘脑-垂体调节激素, 因为胃泌素释放肽 (GRP) 对垂体激素释放的调解中只起微弱作用。
    Gastrin-Releasing Peptide, human (GRP) belongs to the bombesin-like peptide family, and is not a classical hypothalamic-hypophyseal regulatory hormone since it plays only a perfunctory role in the mediation of pituitary hormone release.

  • Dubovy SR, et al. Expression of hypothalamic neurohormones and their receptors in the human eye. Oncotarget. 2017 Jun 3. : https://www.ncbi.nlm.nih.gov/pubmed/28621684

  • 多肽H2N-Val-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr-Val-Leu-Thr-Lys-Met-Tyr-Pro-Arg-Gly-Asn-His-Trp-Ala-Val-Gly-His-Leu-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2.62g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2.36mmol 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4.72mmol DIPEA,2.24mmol 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-Leu-Met-Linker-MBHA Resin

    H2N-Leu-Met-Linker-MBHA Resin

    Fmoc-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Pro-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Pro-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Leu-Pro-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Leu-Pro-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    H2N-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-Met-Linker-MBHA Resin

    Fmoc-Val-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-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-Val-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr(tBu)-Val-Leu-Thr(tBu)-Lys(Boc)-Met-Tyr(tBu)-Pro-Arg(Pbf)-Gly-Asn(Trt)-His(Trt)-Trp(Boc)-Ala-Val-Gly-His(Trt)-Leu-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-Val-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr-Val-Leu-Thr-Lys-Met-Tyr-Pro-Arg-Gly-Asn-His-Trp-Ala-Val-Gly-His-Leu-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,甲基化修饰肽等。

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