400-998-5282
专注多肽 服务科研
400-998-5282
专注多肽 服务科研
GRF (1-29) 酰胺 (sermorelin) 是最短的 GRF 片段，具有完整的生物活性。CAS号（醋酸舍莫林）：114466-38-5。
编号：159254
CAS号：86168-78-7/516482-86-3/114466-38-5
单字母：H2N-YADAIFTNSYRKVLGQLSARKLLQDIMSR-CONH2
GRF (1-29) amide (sermorelin) is the shortest GRF fragment with full biological activity. CAS Number (sermorelin acetate): 114466-38-5.
Growth hormone-releasing factor (GRF) is a peptide fragment of amino acids 1–2 from GHRH (growth hormone-releasing hormone). This 1-29 region is the shortest fully functional fragment of GHRH. GRF is also known as sermorelin.\xa0Sermorelin binds to the growth hormone-releasing hormone receptor (GHRH-R), and acts as a surrogate for GHRH, causing growth hormone secretion.human: H-YADAIFTNSYRKVLGQLSARKLLQDIMSR-NH2rat:\xa0 \xa0 \xa0 \xa0 H-HADAIFTSSYRR I LGQLYARKLLHEIMNR-NH2
| DOI | 名称 | |
|---|---|---|
| 10.1016/s0021-9673(01)01367-x | Set-up of large laboratory-scale chromatographic separations of poly(ethylene glycol) derivatives of the growth hormone-releasing factor 1-29 analogue | 下载 |
| 10.1021/ja021264j | NMR structure of two novel polyethylene glycol conjugates of the human growth hormone-releasing factor, hGRF(1-29)-NH2 | 下载 |
| 10.1111/j.1399-3011.1992.tb00791.x | Potent agonists of growth hormone-releasing hormone. Part I | 下载 |
| 10.1530/eje.0.1500173 | Expression of ghrelin and biological activity of specific receptors for ghrelin and des-acyl ghrelin in human prostate neoplasms and related cell lines | 下载 |
| 10.2165/00063030-199912020-00007 | Sermorelin: a review of its use in the diagnosis and treatment of children with idiopathic growth hormone deficiency | 下载 |
| 10.1111/j.1399-3011.1990.tb00988.x | Synthesis and in vitro and in vivo activity of analogs of growth hormone-releasing hormone (GH-RH) with C-terminal agmatine | 下载 |
| 10.1016/j.ygcen.2014.11.012 | Co-storage and secretion of growth hormone and secretoneurin in retinal ganglion cells | 下载 |
| 10.3168/jds.S0022-0302(02)74263-X | Polymorphism in the bovine growth hormone gene affects endocrine release in dairy calves | 下载 |
多肽H2N-Tyr-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-Met-Ser-Arg-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1.11g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1.0mmol Fmoc-Arg(Pbf)-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2.0mmol DIPEA，0.95mmol 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-Arg(Pbf)-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-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Ala-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Ala-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Asp(OtBu)-Ala-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Asp(OtBu)-Ala-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Ala-Asp(OtBu)-Ala-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
H2N-Ala-Asp(OtBu)-Ala-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-Linker-MBHA Resin
Fmoc-Tyr(tBu)-Ala-Asp(OtBu)-Ala-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-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)-Ala-Asp(OtBu)-Ala-Ile-Phe-Thr(tBu)-Asn(Trt)-Ser(tBu)-Tyr(tBu)-Arg(Pbf)-Lys(Boc)-Val-Leu-Gly-Gln(Trt)-Leu-Ser(tBu)-Ala-Arg(Pbf)-Lys(Boc)-Leu-Leu-Gln(Trt)-Asp(OtBu)-Ile-Met-Ser(tBu)-Arg(Pbf)-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-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-Met-Ser-Arg-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。
以上所有内容，为专肽生物原创内容，请勿发布到其他网站上。
