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萨拉福毒素 C 三氟乙酸盐是一种富含半胱氨酸的肽,结构与内皮素相关,含稳定的二硫键框架。其构象支持受体结合和折叠稳定性分析。该肽广泛用于结构 - 功能和对接研究。应用包括肽工程和结构生物化学。
编号:127986
CAS号:121695-87-2
单字母:H2N-CTCNDMTDEECLNFCHQDVIW-OH
| 编号: | 127986 |
| 中文名称: | 角蝰毒素S6c、Sarafotoxin S6c (Atractaspis engaddensis) |
| 英文名: | Sarafotoxin S6c (Atractaspis engaddensis) |
| CAS号: | 121695-87-2 |
| 单字母: | H2N-CTCNDMTDEECLNFCHQDVIW-OH |
| 三字母: | H2N-Cys-Thr-Cys-Asn-Asp-Met-Thr-Asp-Glu-Glu-Cys-Leu-Asn-Phe-Cys-His-Gln-Asp-Val-Ile-Trp-OH(Disulfide Bridge:Cys1-Cys15 & Cys3-Cys11) |
| 氨基酸个数: | 21 |
| 分子式: | C103H151N27O37S5 |
| 平均分子量: | 2519.78 |
| 精确分子量: | 2517.94 |
| 等电点(PI): | 7.13 |
| pH=7.0时的净电荷数: | 0.09 |
| 酸性基团个数: | -5.08 |
| 碱性基团个数: | 亲水 |
| 平均亲水性: | -0.095238095238095 |
| 疏水性值: | -0.3 |
| 外观与性状: | 白色粉末状固体 |
| 闪点: | 5690 M-1cm-1 |
| 消光系数: | 5500 |
| 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: | 含Cys多肽 |
萨拉福毒素 C 三氟乙酸盐是一种富含半胱氨酸的肽,结构与内皮素相关,含稳定的二硫键框架。其构象支持受体结合和折叠稳定性分析。该肽广泛用于结构 - 功能和对接研究。应用包括肽工程和结构生物化学。
Sarafotoxin C trifluoroacetate salt is a cysteine-rich peptide structurally related to endothelins, bearing a stabilized disulfide framework. Its conformation supports receptor-binding and fold-stability analysis. The peptide is widely used in structure-function and docking studies. Applications include peptide engineering and structural biochemistry.
沙漠角蝰毒肽 C 是一种强效蛇毒多肽,结构与内皮素家族多肽相关。二硫键稳定结构将多肽锁定为紧凑、受体活性构象。疏水与带电残基形成明确结合表面。研究人员用其探究血管活性肽家族内结构‑活性关系与受体相互作用机制。
Sarafotoxin C is a potent snake-venom peptide structurally related to endothelin-family peptides. Disulfide-stabilized architecture locks the peptide into a compact, receptor-active conformation. Hydrophobic and charged residues create defined binding surfaces. Researchers employ it to probe structure–activity relationships within vasoactive peptide families and receptor-interaction mechanisms.
萨拉弗毒素 6c 具有高度约束的二硫键结构,与内皮素样结构基序相似。疏水簇集有助于受体结合研究。构象刚性为毒素选择性提供了见解。该多肽广泛用于构效分析和比较毒液研究。
Sarafotoxin 6c features tightly constrained disulfide linkages resembling endothelin-like structural motifs. Hydrophobic clustering aids receptor-binding studies. Conformational rigidity provides insights into toxin selectivity. The peptide is widely used in structure–activity analysis and comparative venom research.
Highly selective ET-B receptor agonist.
高选择性ET-B受体激动剂
Sarafotoxin C is a peptide from the venom of the spider Phoneutria nigriventer that has been shown to have potent inhibitory properties on endothelin-1. Sarafotoxin C is able to block intracellular Ca2+ levels and signal pathways, leading to decreased levels of endothelin-1 as well as other inflammatory mediators. Sarafotoxin C has also been shown to have an anti-inflammatory effect in bowel disease, which may be due to its ability to inhibit the production of cytokines and prostaglandins. The biological properties of sarafotoxin C are related to its inhibition of polymerase chain reaction (PCR) amplification of DNA. This inhibition is due to the binding of sarafotoxin C with endothelin receptors on DNA, which prevents DNA polymerase from attaching. Endothelin-a receptor activity can also be inhibited by sarafotoxin C through enzymatic inactivation. Sarafot
Sarafotoxin S6c, sourced from the venom of the Atractaspis engaddensis snake family, is one of four (S6a-d) isopeptides of the Sarafotoxins. This product is a synthetically produced toxin, containing disulfide bonds between Cys1-Cys15 and Cys3-Cys11.\nDue to their structural and functional homology to the endothelin peptides, Sarafotoxins can enhance vasoconstriction through stimulating the class A G-protein-coupled, endothelin ETA and ETB receptors. This in turn leads to left ventricular dysfunction and bronchoconstriction. Compared to the sarafotoxin isopeptide S6b, S6c is less toxic with a 100 to 10,000-fold reduced affinity for the ETA receptor, therefore acts as a selective agonist to the ETB receptor. One study demonstrated that when sarafotoxin 6c was used to activate ETB receptors in rats there was an increase in arterial pressure, known as S6c-induced hypertension.\nAs the upregulation of Endothelin-1 (ET-1) is related to circulatory-system diseases, the interaction between ET-1 and its receptors is highly important for development of endothelin receptor antagonist treatments. Sarafotoxin S6c can be used as a pharmacological reagent to study these interactions.
多肽H2N-Cys-Thr-Cys-Asn-Asp-Met-Thr-Asp-Glu-Glu-Cys-Leu-Asn-Phe-Cys-His-Gln-Asp-Val-Ile-Trp-COOH的合成步骤:
1、合成CTC树脂:称取2.22g CTC Resin(如初始取代度约为0.4mmol/g)和1.07mmol Fmoc-Trp(Boc)-OH于反应器中,加入适量DCM溶解氨基酸(需要注意,此时CTC树脂体积会增大好几倍,避免DCM溶液过少),再加入2.66mmol DIPEA(Mw:129.1,d:0.740g/ml),反应2-3小时后,可不抽滤溶液,直接加入1ml的HPLC级甲醇,封端半小时。依次用DMF洗涤2次,甲醇洗涤1次,DCM洗涤一次,甲醇洗涤一次,DCM洗涤一次,DMF洗涤2次(这里使用甲醇和DCM交替洗涤,是为了更好地去除其他溶质,有利于后续反应)。得到 Fmoc-Trp(Boc)-CTC Resin。结构图如下:

2、脱Fmoc: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-Trp(Boc)-CTC 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2.66mmol Fmoc-Ile-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5.33mmol DIPEA,2.53mmol 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-Ile-Trp(Boc)-CTC 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-Ile-Trp(Boc)-CTC Resin
Fmoc-Val-Ile-Trp(Boc)-CTC Resin
H2N-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Asn(Trt)-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Asn(Trt)-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Cys(Trt)-Asn(Trt)-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Cys(Trt)-Asn(Trt)-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Thr(tBu)-Cys(Trt)-Asn(Trt)-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
H2N-Thr(tBu)-Cys(Trt)-Asn(Trt)-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC Resin
Fmoc-Cys(Trt)-Thr(tBu)-Cys(Trt)-Asn(Trt)-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC 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-Cys(Trt)-Thr(tBu)-Cys(Trt)-Asn(Trt)-Asp(OtBu)-Met-Thr(tBu)-Asp(OtBu)-Glu(OtBu)-Glu(OtBu)-Cys(Trt)-Leu-Asn(Trt)-Phe-Cys(Trt)-His(Trt)-Gln(Trt)-Asp(OtBu)-Val-Ile-Trp(Boc)-CTC 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-Cys-Thr-Cys-Asn-Asp-Met-Thr-Asp-Glu-Glu-Cys-Leu-Asn-Phe-Cys-His-Gln-Asp-Val-Ile-Trp-COOH。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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