Neuropeptide originally isolated from porcine upper small intestine.
编号:195446
CAS号:88813-36-9
单字母:H2N-GWTLNSAGYLLGPHAIDNHRSFHDKYGLA-NH2
编号: | 195446 |
中文名称: | 甘丙肽Galanin, porcine |
英文名: | Galanin, porcine |
CAS号: | 88813-36-9 |
单字母: | H2N-GWTLNSAGYLLGPHAIDNHRSFHDKYGLA-NH2 |
三字母: | H2N N端氨基 -Gly甘氨酸 -Trp色氨酸 -Thr苏氨酸 -Leu亮氨酸 -Asn天冬酰胺 -Ser丝氨酸 -Ala丙氨酸 -Gly甘氨酸 -Tyr酪氨酸 -Leu亮氨酸 -Leu亮氨酸 -Gly甘氨酸 -Pro脯氨酸 -His组氨酸 -Ala丙氨酸 -Ile异亮氨酸 -Asp天冬氨酸 -Asn天冬酰胺 -His组氨酸 -Arg精氨酸 -Ser丝氨酸 -Phe苯丙氨酸 -His组氨酸 -Asp天冬氨酸 -Lys赖氨酸 -Tyr酪氨酸 -Gly甘氨酸 -Leu亮氨酸 -Ala丙氨酸 -NH2C端酰胺化 |
氨基酸个数: | 29 |
分子式: | C146H213N43O40 |
平均分子量: | 3210.52 |
精确分子量: | 3208.6 |
等电点(PI): | 10.67 |
pH=7.0时的净电荷数: | 3.68 |
酸性基团个数: | 1.29 |
碱性基团个数: | 疏水 |
平均亲水性: | -0.50416666666667 |
疏水性值: | -0.42 |
外观与性状: | 白色粉末状固体 |
消光系数: | 8480 |
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 |
储存条件: | 负80℃至负20℃ |
标签: | 甘丙肽/甘丙样肽 |
Neuropeptide originally isolated from porcine upper small intestine.
DOI | 名称 | |
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10.1016/j.autneu.2004.04.002 | Coexistence of non-adrenergic non-cholinergic inhibitory and excitatory neurotransmitters in a large neuronal subpopulation in the vaginal segment of the chicken oviduct | 下载 |
10.14670/HH-20.509 | Response of the gut neuroendocrine system of Leuciscus cephalus (L.) to the presence of Pomphorhynchus laevis Müller, 1776 (Acanthocephala) | 下载 |
10.3354/dao066245 | Histopathology, ultrastructure and immunohistochemistry of Coregonus lavaretus hearts naturally infected with Ichthyocotylurus erraticus (Trematoda) | 下载 |
10.1073/pnas.87.18.7105 | PD134308, a selective antagonist of cholecystokinin type B receptor, enhances the analgesic effect of morphine and synergistically interacts with intrathecal galanin to depress spinal nociceptive reflexes | 下载 |
10.1111/j.1365-2761.2007.00833.x | Selected pathological, immunohistochemical and ultrastructural changes associated with an infection by Diphyllobothrium dendriticum (Nitzsch, 1824) (Cestoda) plerocercoids in Coregonus lavaretus (L.) (Coregonidae) | 下载 |
10.1111/j.1365-2982.2010.01529.x | The chemical code of porcine enteric neurons and the number of enteric glial cells are altered by dietary probiotics | 下载 |
10.1002/cne.23131 | Galanin gene expression and effects of its knock-down on the development of the nervous system in larval zebrafish | 下载 |
10.1111/ahe.12179 | Galanin is Co-Expressed with Substance P, Calbindin and Corticotropin-Releasing Factor (CRF) in The Enteric Nervous System of the Wild Boar (Sus scrofa) Small Intestine | 下载 |
10.1016/0014-5793(83)80033-7 | Galanin - a novel biologically active peptide from porcine intestine | 下载 |
多肽H2N-Gly-Trp-Thr-Leu-Asn-Ser-Ala-Gly-Tyr-Leu-Leu-Gly-Pro-His-Ala-Ile-Asp-Asn-His-Arg-Ser-Phe-His-Asp-Lys-Tyr-Gly-Leu-Ala-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2.45g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2.21mmol Fmoc-Ala-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4.41mmol DIPEA,2.09mmol 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-Ala-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-Ala-Linker-MBHA Resin
Fmoc-Leu-Ala-Linker-MBHA Resin
H2N-Leu-Ala-Linker-MBHA Resin
Fmoc-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Leu-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Leu-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Thr(tBu)-Leu-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Thr(tBu)-Leu-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Trp(Boc)-Thr(tBu)-Leu-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
H2N-Trp(Boc)-Thr(tBu)-Leu-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-Linker-MBHA Resin
Fmoc-Gly-Trp(Boc)-Thr(tBu)-Leu-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-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-Gly-Trp(Boc)-Thr(tBu)-Leu-Asn(Trt)-Ser(tBu)-Ala-Gly-Tyr(tBu)-Leu-Leu-Gly-Pro-His(Trt)-Ala-Ile-Asp(OtBu)-Asn(Trt)-His(Trt)-Arg(Pbf)-Ser(tBu)-Phe-His(Trt)-Asp(OtBu)-Lys(Boc)-Tyr(tBu)-Gly-Leu-Ala-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-Gly-Trp-Thr-Leu-Asn-Ser-Ala-Gly-Tyr-Leu-Leu-Gly-Pro-His-Ala-Ile-Asp-Asn-His-Arg-Ser-Phe-His-Asp-Lys-Tyr-Gly-Leu-Ala-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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