编号: | 206125 |
中文名称: | 棕榈酸-VVVAAAGCGKSLSRHDHIHHHWWWF |
单字母: | Palmiticacid-VVVAAAGCGKSLSRHDHIHHHWWWF-OH |
三字母: | Palmiticacid 棕榈酸修饰 -Val缬氨酸 -Val缬氨酸 -Val缬氨酸 -Ala丙氨酸 -Ala丙氨酸 -Ala丙氨酸 -Gly甘氨酸 -Cys半胱氨酸 -Gly甘氨酸 -Lys赖氨酸 -Ser丝氨酸 -Leu亮氨酸 -Ser丝氨酸 -Arg精氨酸 -His组氨酸 -Asp天冬氨酸 -His组氨酸 -Ile异亮氨酸 -His组氨酸 -His组氨酸 -His组氨酸 -Trp色氨酸 -Trp色氨酸 -Trp色氨酸 -Phe苯丙氨酸 -OHC端羧基 |
氨基酸个数: | 25 |
分子式: | C153H220O31N42S1 |
平均分子量: | 3175.71 |
精确分子量: | 3173.66 |
等电点(PI): | 11.66 |
pH=7.0时的净电荷数: | 3.15 |
平均亲水性: | -0.70434782608696 |
疏水性值: | -0.06 |
外观与性状: | 粉末状固体 |
消光系数: | 16500 |
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: | 烷基化肽 |
烷基化肽-说明
专肽生物可提供多肽烷基化修饰,增加多肽一端的疏水性,例如常见的C18,C16,C14,C12,以及C6等,也可根据客户要求,接其他长度的烷基化链。
多肽Palmiticacid-Val-Val-Val-Ala-Ala-Ala-Gly-Cys-Gly-Lys-Ser-Leu-Ser-Arg-His-Asp-His-Ile-His-His-His-Trp-Trp-Trp-Phe-COOH的合成步骤:
1、合成CTC树脂:称取0.34g CTC Resin(如初始取代度约为0.93mmol/g)和0.38mmol Fmoc-Phe-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0.95mmol 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-Phe-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-Phe-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0.95mmol Fmoc-Trp(Boc)-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1.9mmol DIPEA,0.9mmol 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-Trp(Boc)-Phe-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-Trp(Boc)-Phe-CTC Resin
Fmoc-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Val-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Val-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Val-Val-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
H2N-Val-Val-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin
Fmoc-Val-Val-Val-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-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-Val-Val-Val-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTC Resin,结构如下:
5、棕榈酸反应连接:在上述树脂中,加入适当DMF后,再加入0.95mmol 棕榈酸到树脂中,再加入1.9mmol DIPEA、0.9mmol HBTU,鼓氮气反应30分钟。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Palmiticacid-Val-Val-Val-Ala-Ala-Ala-Gly-Cys(Trt)-Gly-Lys(Boc)-Ser(tBu)-Leu-Ser(tBu)-Arg(Pbf)-His(Trt)-Asp(OtBu)-His(Trt)-Ile-His(Trt)-His(Trt)-His(Trt)-Trp(Boc)-Trp(Boc)-Trp(Boc)-Phe-CTCResin。 结构如下:
6、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Palmiticacid-Val-Val-Val-Ala-Ala-Ala-Gly-Cys-Gly-Lys-Ser-Leu-Ser-Arg-His-Asp-His-Ile-His-His-His-Trp-Trp-Trp-Phe-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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