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169332-61-0,四肽Apopain Substrate,Ac-Asp-Glu-Val-Asp-AMC,Ac-DEVD-AMC,杭州專肽生物的產(chǎn)品

Caspase 3 (Apopain) Substrate 1m, fluorogenic

A continuous fluorometric assay employing Ac-DEVD-AMC has been developed for the measurement of caspase-3, a cysteine protease also called apopain, Yama or CPP-32. The design of this substrate Ac-DEVD-AMC was based on the substrate motif that has been use

編號：145638

CAS號：169332-61-0

單字母：Ac-DEVD-AMC

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  • 編號:145638
    中文名稱:Caspase 3 (Apopain) Substrate 1m, fluorogenic
    英文名:Caspase 3 (Apopain) Substrate 1m, fluorogenic
    英文同義詞:Apopain Substrate
    CAS號:169332-61-0
    單字母:Ac-DEVD-AMC
    三字母:Ac

    N端乙?；舛?/p>-Asp

    天冬氨酸

    -Glu

    谷氨酸

    -Val

    纈氨酸

    -Asp

    天冬氨酸

    -AMC

    7-氨基-4-甲基香豆素

    氨基酸個數(shù):4
    分子式:C30H37O13N5
    平均分子量:675.64
    精確分子量:675.24
    等電點(diǎn)(PI):-
    pH=7.0時的凈電荷數(shù):-3
    平均親水性:1.875
    疏水性值:-1.58
    外觀與性狀:白色粉末狀固體
    消光系數(shù):-
    來源:人工化學(xué)合成，僅限科學(xué)研究使用，不得用于人體。
    純度:95%、98%
    鹽體系:可選TFA、HAc、HCl或其它
    生成周期:2-3周
    儲存條件:負(fù)80℃至負(fù)20℃
    標(biāo)簽:AMC修飾肽   

  • A continuous fluorometric assay employing Ac-DEVD-AMC has been developed for the measurement of caspase-3, a cysteine protease also called apopain, Yama or CPP-32. The design of this substrate Ac-DEVD-AMC was based on the substrate motif that has been used successfully with caspase-1, using the poly(ADP-ribose) polymerase cleavage site P?-P? tetrapeptide.

    多肽熒光標(biāo)記由于沒有放射性，實(shí)驗(yàn)操作簡單。因此，目前在生物學(xué)研究中多肽熒光標(biāo)記應(yīng)用非常廣泛，多肽熒光標(biāo)記方法與熒光試劑的結(jié)構(gòu)有關(guān)系，對于有游離羧基的采用的方法與接多肽反應(yīng)相同，也采用HBTU/HOBt/DIEA方法連接。 在N端標(biāo)記FITC的多肽需經(jīng)歷環(huán)化作用來形成熒光素，通常會伴有最后一個氨基酸的去除，但當(dāng)有一個間隔器如氨基己酸，或者是通過非酸性環(huán)境將目的多肽從樹脂上切下來時，這種情況可避免在切割的過程中被TFA切割掉。
            人們利用利用熒光標(biāo)記的多肽來檢測目標(biāo)蛋白的活性，并將 其發(fā)展的高通量活性篩選方法應(yīng)用于疾病治療靶點(diǎn)蛋白的藥物篩選和藥物開發(fā)（例如，各種激 酶、磷酸酶、肽酶等）。
            專肽生物能夠提供技術(shù)成熟的各種熒光標(biāo)記多肽。
     

     

    下面是一些常見的多肽修飾熒光物質(zhì)結(jié)構(gòu)：




    FITC標(biāo)記
     

     

          FITC(異硫氰酸熒光素)具有比較高的活性，我們公司可以通過兩種方式將FITC標(biāo)記于多肽 上：(1) 將FITC標(biāo)記于賴氨酸（Lys）或被選擇性地脫保護(hù)的鳥氨酸（ornithine）側(cè)鏈氨基 上；(2) 將FITC標(biāo)記于多肽N端氨基。

     

          當(dāng)在N端標(biāo)記時，建議在最后一個氨基和由異硫氰酸酯與氨基反應(yīng)產(chǎn)生的硫脲鍵之間引入 烷基間隔器（alkyl spacer），如氨基己酸（Ahx）。鏈接切割需要酸性環(huán)境，在N端標(biāo)記FITC 的多肽需經(jīng)歷環(huán)化作用來形成熒光素，通常會伴有最后一個氨基酸的去除，但當(dāng)有一個間隔器 如氨基己酸，或者是通過非酸性環(huán)境將目的肽從樹脂上切下來時，這種情況可避免?？臻g位阻 被認(rèn)為是在熒光染料前使用Ahx的主要原因，而不是為什么FITC不能直接偶聯(lián)在多肽上的原因。

     

          Ahx或b-Ala均可作為間隔器用于FITC標(biāo)記的多肽上。

     

     

     



     

    普通熒光修飾

     

    熒光修飾中文名稱 N端 N端帶有l(wèi)inker
    生物素標(biāo)記多肽 Biotin- Biotin-Ahx-
    異硫氰酸熒光素 FITC-   FITC-Ahx-  
    5-羧基熒光素 5-FAM- 5-FAM-Ahx- 
    丹磺酰熒光素 Dansyl- Dansyl-Ahx- 
    5-羧基四甲基羅丹明 TMR-  （TAMRA-） TMR-Ahx-  （TAMRA-Ahx-） 

    通過Lys側(cè)鏈氨基連接的熒光修飾

     

    多肽N端 多肽序列中間 N端帶有l(wèi)inker
    生物素標(biāo)記多肽 Biotin- 多肽C端
    Lys(Biotin)-  -Lys(Biotin)-- -Lys(Biotin) 
    Lys(FITC)- -Lys(FITC)-  -Lys(FITC)
    Lys(5-FAM)- -Lys(5-FAM)- -Lys(5-FAM)
    Lys(Dansyl)-  -Lys(Dansyl)- -Lys(Dansyl)
    Lys(TMR)- -Lys(TMR)-  -Lys(TMR)
    Lys(Dnp)- -Lys(Dnp)-  -Lys(Dnp)



    專肽常做的熒光物質(zhì)的激發(fā)光波長和發(fā)射光波長?？晒﹨⒖歼x擇：
     

    熒光基團(tuán) Ex（nm） Em（nm） 熒光基團(tuán) Ex（nm） Em（nm）
    羥基香豆素 325 386 R-phycoerythrin (PE) (489) 565 578
    丹磺酰氯 340 578 Rhodamine Red-X 560 580
    AMC 345 445 Tamara 565 580
    甲氧基香豆素 360 410 Alexa fluor 555 556 573
    Alexa fluor 系列 345 442 Alexa fluor 546 556 573
    氨基香豆素 350 445 Rox 575 602
    Dabcyl 453 - Alexa fluor 568 578 603
    Cy2 490 510 Texas Red 589 615
    FAM 495 517 Alexa fluor 594 590 617
    Alexa fluor 488 494 517 Alexa fluor 621 639
    FITC 495 519 Alexa fluor 633 650 668
    Alexa fluor 430 430 545 Cy5 (625) 650 670
    5-FAM 492 518 Alexa fluor 660 663 690
    Alexa fluor 532 530 530 Cy5.5 675 694
    HEX 535 556 TruRed 490; 675 695
    5-TAMRA 542 568 Alexa fluor 680 679 702
    Cy3 550 570 Cy7 743 767
    TRITC 547 572 Cy3.5 581

    596

     

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  • 多肽Ac-Asp-Glu-Val-Asp-AMC的合成步驟：

    1、合成CTC樹脂：稱取2.97g CTC Resin（如初始取代度約為0.41mmol/g）和1.46mmol Fmoc-Asp(OtBu)-OH于反應(yīng)器中，加入適量DCM溶解氨基酸（需要注意，此時CTC樹脂體積會增大好幾倍，避免DCM溶液過少），再加入3.65mmol DIPEA（Mw：129.1,d：0.740g/ml），反應(yīng)2-3小時后，可不抽濾溶液，直接加入1ml的HPLC級甲醇，封端半小時。依次用DMF洗滌2次，甲醇洗滌1次，DCM洗滌一次，甲醇洗滌一次，DCM洗滌一次，DMF洗滌2次（這里使用甲醇和DCM交替洗滌，是為了更好地去除其他溶質(zhì)，有利于后續(xù)反應(yīng)）。得到  Fmoc-Asp(OtBu)-CTC Resin。結(jié)構(gòu)圖如下：

    2、脫Fmoc：加3倍樹脂體積的20%Pip/DMF溶液，鼓氮?dú)?0分鐘，然后2倍樹脂體積的DMF 洗滌5次。得到 H2N-Asp(OtBu)-CTC Resin 。（此步驟脫除Fmoc基團(tuán)，茚三酮檢測為藍(lán)色，Pip為哌啶）。結(jié)構(gòu)圖如下：

    3、縮合：取3.65mmol Fmoc-Val-OH 氨基酸，加入到上述樹脂里，加適當(dāng)DMF溶解氨基酸，再依次加入7.31mmol DIPEA，3.47mmol HBTU。反應(yīng)30分鐘后，取小樣洗滌，茚三酮檢測為無色。用2倍樹脂體積的DMF 洗滌3次樹脂。（洗滌樹脂，去掉殘留溶劑，為下一步反應(yīng)做準(zhǔn)備）。得到Fmoc-Val-Asp(OtBu)-CTC Resin。氨基酸：DIPEA：HBTU：樹脂=3：6：2.85：1（摩爾比）。結(jié)構(gòu)圖如下：

    4、依次循環(huán)步驟二、步驟三，依次得到

    H2N-Val-Asp(OtBu)-CTC Resin

    Fmoc-Glu(OtBu)-Val-Asp(OtBu)-CTC Resin

    H2N-Glu(OtBu)-Val-Asp(OtBu)-CTC Resin

    Fmoc-Asp(OtBu)-Glu(OtBu)-Val-Asp(OtBu)-CTC Resin

    以上中間結(jié)構(gòu)，均可在專肽生物多肽計(jì)算器-多肽結(jié)構(gòu)計(jì)算器中，一鍵畫出。

    最后再經(jīng)過步驟二得到 H2N-Asp(OtBu)-Glu(OtBu)-Val-Asp(OtBu)-CTC Resin，結(jié)構(gòu)如下：

    5、乙酸酐反應(yīng)連接：在上述樹脂中，加入適當(dāng)DMF后，再加入3.65mmol 乙酸酐到樹脂中，再加入7.31mmol DIPEA、3.47mmol HBTU，鼓氮?dú)夥磻?yīng)30分鐘。用2倍樹脂體積的DMF 洗滌3次樹脂（洗滌樹脂，去掉殘留溶劑，為下一步反應(yīng)做準(zhǔn)備）。 得到Ac-Asp(OtBu)-Glu(OtBu)-Val-Asp(OtBu)-CTC Resin。 結(jié)構(gòu)如下：

    6、全保護(hù)切割：配置0.5%TFA/DCM溶液，溶液體積約為樹脂體積的3倍。再次用DCM洗滌樹脂2遍（去除殘留DMF），后將配置好的溶液倒入到反應(yīng)器中，反應(yīng)30分鐘。抽濾樹脂，收集濾液（此時多肽已經(jīng)從樹脂上分離，存在于濾液中）。多肽序列為 Ac-Asp(OtBu)-Glu(OtBu)-Val-Asp(OtBu)-CTC Resin。 在濾液中添加DIEPA，調(diào)PH至7-8。用飽和NaHCO3洗滌濾液，分離出DCM層溶液?？蛇m當(dāng)旋蒸DCM層溶液，減少有機(jī)溶劑。再次加入1或2倍體積的乙酸乙酯，用稀HCl溶液調(diào)PH至微酸性，將多肽從DCM層萃取到乙酸乙酯層。用飽和NaCl洗滌2次乙酸乙酯層。用無水硫酸鎂吸收乙酸乙酯層的水分。通過減壓旋蒸，直接將乙酸乙酯完全旋蒸掉，得到晶體狀固體多肽，用于下一步C端反應(yīng)?；蛲ㄟ^減壓旋蒸保留適量乙酸乙酯的溶液體積，加入冰乙醚析出 多肽，然后對多肽進(jìn)行烘干操作即可用于下一步C端反應(yīng)。Ac-Asp(OtBu)-Glu(OtBu)-Val-Asp(OtBu)-COOH的結(jié)構(gòu)圖如下。

    7、7-氨基-4-甲基香豆素反應(yīng)連接：在上述樹脂中，加入適當(dāng)DMF后，再加入3.65mmol 7-氨基-4-甲基香豆素到樹脂中，再加入7.31mmol DIPEA、3.47mmol HBTU，鼓氮?dú)夥磻?yīng)30分鐘。用2倍樹脂體積的DMF 洗滌3次樹脂（洗滌樹脂，去掉殘留溶劑，為下一步反應(yīng)做準(zhǔn)備）。 得到 Ac-Asp(OtBu)-Glu(OtBu)-Val-Asp(OtBu)-AMC。 結(jié)構(gòu)如下：

    8、切割：6倍樹脂體積的切割液（或每1g樹脂加8ml左右的切割液），搖床搖晃 2小時，過濾掉樹脂，用冰無水乙醚沉淀濾液，并用冰無水乙醚洗滌沉淀物3次，最后將沉淀物放真空干燥釜中，常溫干燥24小試，得到粗品Ac-Asp-Glu-Val-Asp-AMC。結(jié)構(gòu)圖見產(chǎn)品結(jié)構(gòu)圖。

    切割液選擇：1）TFA：H2O=95%：5%、TFA：H2O=97.5%：2.5%

    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%

    （前兩種適合沒有容易氧化的氨基酸，例如Trp、Cys、Met。第三種適合幾乎所有的序列。）

    9、純化凍干：使用液相色譜純化，收集目標(biāo)峰液體，進(jìn)行凍干，獲得蓬松的粉末狀固體多肽。不過這時要取小樣復(fù)測下純度 是否目標(biāo)純度。

    10、最后總結(jié)：

    杭州專肽生物技術(shù)有限公司（ALLPEPTIDE http://amynixphotography.com）主營定制多肽合成業(yè)務(wù)，提供各類長肽，短肽，環(huán)肽，提供各類修飾肽，如：熒光標(biāo)記修飾（CY3、CY5、CY5.5、CY7、FAM、FITC、Rhodamine B、TAMRA等），功能基團(tuán)修飾肽（疊氮、炔基、DBCO、DOTA、NOTA等），同位素標(biāo)記肽（N15、C13），訂書肽（Stapled Peptide）,脂肪酸修飾肽（Pal、Myr、Ste），磷酸化修飾肽（P-Ser、P-Thr、P-Tyr），環(huán)肽（酰胺鍵環(huán)肽、一對或者多對二硫鍵環(huán)），生物素標(biāo)記肽，PEG修飾肽，甲基化修飾肽

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