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162558-10-3,褪黑素Melanocyte Protein PMEL 17 (185-193) (human, bo,H2N-Ile-Thr-Asp-Gln-Val-Pro-Phe-Ser-Val-COOH,H2N-ITDQVPFSV-OH,杭州专肽生物的产品

褪黑素Melanocyte Protein PMEL 17 (185-193) (human, bovine, mouse)

作为KTWGQYWQV,ITDQVPFSV是一种gp100表位,在HLA-A2的背景下被体内肿瘤浸润淋巴细胞(TIL)识别。PMEL 17可能是一种黑色素生成酶。

编号:143927

CAS号:162558-10-3

单字母:H2N-ITDQVPFSV-OH

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  • 编号:143927
    中文名称:褪黑素Melanocyte Protein PMEL 17 (185-193) (human, bovine, mouse)
    英文名:Melanocyte Protein PMEL 17 (185-193) (human, bovine, mouse)
    英文同义词:Melanocyte Protein PMEL 17 (185-193) (human, bovine, mouse), ME20M/ME20S (130-138) (human), Melanoma-Associated ME20 Antigen (185-193) (human, bovine, mouse), Melanocyte Lineage-Specific Antigen GP100 (185-193) (human, bovine, mouse), ME20-M/ME20-S (130-1
    CAS号:162558-10-3
    单字母:H2N-ITDQVPFSV-OH
    三字母:H2N

    N端氨基:N-terminal amino group。在肽或多肽链中含有游离a-氨基的氨基酸一端。在表示氨基酸序列时,通常将N端放在肽链的左边。

    -Ile

    L-异亮氨酸:isoleucine。系统命名为(2S)-氨基-(3R)-甲基戊酸。是编码氨基酸。有两个手性碳原子,是哺乳动物的必需氨基酸。符号:I,Ile。

    -Thr

    L-苏氨酸:threonine。系统命名为(2S)-氨基-(3R)-羟基丁酸。有两个手性中心,是编码氨基酸。是哺乳动物的必需氨基酸。符号:T,Thr。

    -Asp

    L-天冬氨酸:aspartic acid。系统命名为(2S)-氨基-丁二酸。是编码氨基酸,又是神经递质。符号:D,Asp。D-天冬氨酸存在于多种细菌的细胞壁和短杆菌肽A中。

    -Gln

    L-谷氨酰胺:glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸,是编码氨基酸。符号:GIn,Q。

    -Val

    L-缬氨酸:valine。系统命名为(2S)-氨基-3-甲基丁酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号:V,Val。在某些放线菌素如缬霉素中存在 D-缬氨酸。

    -Pro

    L-脯氨酸:proline。系统命名为吡咯烷-(2S)-羧酸。为亚氨基酸。是编码氨基酸。在肽链中有特殊作用,如易形成顺式的肽键等。符号:P,Pro。

    -Phe

    L-苯丙氨酸:phenylalanine。系统命名为(2S)-氨基-3-苯基丙酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号:F,Phe。

    -Ser

    L-丝氨酸:serine。系统命名为(2S)-氨基-3-羟基丙酸。是编码氨基酸。因可从蚕丝中获得而得名。符号:S,Ser。在丝原蛋白及某些抗菌素中含有 D-丝氨酸。

    -Val

    L-缬氨酸:valine。系统命名为(2S)-氨基-3-甲基丁酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号:V,Val。在某些放线菌素如缬霉素中存在 D-缬氨酸。

    -OH

    C端羧基:C-terminal carboxyl group。在肽或多肽链中含有游离羧基的氨基酸一端。在表示氨基酸序列时,通常将C端放在肽链的右边。

    氨基酸个数:9
    分子式:C46H72N10O15
    平均分子量:1005.12
    精确分子量:1004.52
    等电点(PI):6.26
    pH=7.0时的净电荷数:-0.02
    酸性基团个数:-1
    碱性基团个数:疏水
    平均亲水性:-0.525
    疏水性值:0.62
    外观与性状:白色粉末状固体
    闪点:0 M-1cm-1
    消光系数:-
    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:黑色素(Melanin)相关肽   

  • 作为KTWGQYWQV,ITDQVPFSV是一种gp100表位,在HLA-A2的背景下被体内肿瘤浸润淋巴细胞(TIL)识别。PMEL 17可能是一种黑色素生成酶。

    As KTWGQYWQV, ITDQVPFSV is a gp100 epitope that is recognized in the context of HLA-A2 by tumor-infiltrating lymphocytes (TIL) in vivo. PMEL 17 could be a melanogenic enzyme.

    一种黑色素生成酶,在HLA-A2的背景下被体内肿瘤冲洗淋巴细胞(TIL)识别。

    A melanogenic enzyme that is recognized in the context of HLA-A2 by tumo-rinfiltrating lymphocytes (TIL) in vivo.

    Peptide H-ITDQVPFSV-OH is a Research Peptide with significant interest within the field academic and medical research. Recent citations using H-ITDQVPFSV-OH include the following: Functional characterization of CTL against gp100 altered peptide ligands SO Dionne, MH Smith, FM Marincola - Cancer Immunology , 2003 - Springerhttps://link.springer.com/article/10.1007/s00262-002-0358-3 Antigen presentation of a modified tumor-derived peptide by tumor infiltrating lymphocytes SO Dionne, MH Smith, FM Marincola, DF Lake - Cellular immunology, 2001 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0008874901918933 Induction of circulating tumor-reactive CD8+ T cells after vaccination of melanoma patients with the gp100209-2M peptide SL Meijer, A Dols, SM Jensen, HM Hu - Journal of , 2007 - journals.lww.comhttps://journals.lww.com/immunotherapy-journal/fulltext/2007/07000/Adoptive_Cellular_Therapy_With_Tumor_Vaccine.00008.aspx Increased immunogenicity of an anchor-modified tumor-associated antigen is due to the enhanced stability of the peptide/MHC complex: implications for vaccine OY Borbulevych , TK Baxter, Z Yu - The Journal of , 2005 - journals.aai.orghttps://journals.aai.org/jimmunol/article/174/8/4812/1745 An HLA-A2 polyepitope vaccine for melanoma immunotherapy L Mateo, J Gardner, Q Chen, C Schmidt - The Journal of , 1999 - journals.aai.orghttps://journals.aai.org/jimmunol/article/163/7/4058/105313 Recombinant Virus Vaccination against"Self"Â\x9d Antigens UsingAnchor-fixed Immunogens KR Irvine, MR Parkhurst, EP Shulman, JP Tupesis - Cancer research, 1999 - AACRhttps://aacrjournals.org/cancerres/article-abstract/59/11/2536/505166 Destructive cleavage of antigenic peptides either by the immunoproteasome or by the standard proteasome results in differential antigen presentation J Chapiro, S Claverol, F Piette, W Ma - The Journal of , 2006 - journals.aai.orghttps://journals.aai.org/jimmunol/article/176/2/1053/73604 Peptide-specific CD8+ T-cell evolution in vivo: Response to peptide vaccination with Melan-A/MART-1 E Jager, H Höhn, A Necker, R Förster - journal of cancer, 2002 - Wiley Online Libraryhttps://onlinelibrary.wiley.com/doi/abs/10.1002/ijc.10165 Phenotypic and functional maturation of tumor antigen-reactive CD8+ T lymphocytes in patients undergoing multiple course peptide vaccination DJ Powell Jr, SA Rosenberg - Journal of immunotherapy, 2004 - journals.lww.comhttps://journals.lww.com/immunotherapy-journal/fulltext/2004/01000/Long_Term_Survival_of_Anti_Tumor_Lymphocytes.4.aspx Immunogenicity for CD8+ and CD4+ T cells of 2 formulations of an incomplete freund\s adjuvant for multipeptide melanoma vaccines CL Slingluff , GR Petroni , ME Smolkin - Journal of , 2010 - journals.lww.comhttps://journals.lww.com/immunotherapy-journal/fulltext/2010/07000/immunogenicity_for_cd8__and_cd4__t_cells_of_2.8.aspx Generation of melanoma-specific cytotoxic T lymphocytes for allogeneic immunotherapy A Nolte, C Scheffold, J Slotty, C Huenefeld - Journal of , 2003 - journals.lww.comhttps://journals.lww.com/immunotherapy-journal/fulltext/2003/05000/Response_Rates_of_Patients_With_Metastatic.9.aspx

  • DOI名称
    10.1615/critrevimmunol.v18.i1-2.30Identification of peptides for immunotherapy of cancer. It is worth the effort下载
  • 多肽H2N-Ile-Thr-Asp-Gln-Val-Pro-Phe-Ser-Val-COOH的合成步骤:

    1、合成CTC树脂:称取1.76g CTC Resin(如初始取代度约为1.04mmol/g)和2.2mmol Fmoc-Val-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5.49mmol 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-Val-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-Val-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5.49mmol Fmoc-Ser(tBu)-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10.98mmol DIPEA,5.22mmol 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-Ser(tBu)-Val-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-Ser(tBu)-Val-CTC Resin

    Fmoc-Phe-Ser(tBu)-Val-CTC Resin

    H2N-Phe-Ser(tBu)-Val-CTC Resin

    Fmoc-Pro-Phe-Ser(tBu)-Val-CTC Resin

    H2N-Pro-Phe-Ser(tBu)-Val-CTC Resin

    Fmoc-Val-Pro-Phe-Ser(tBu)-Val-CTC Resin

    H2N-Val-Pro-Phe-Ser(tBu)-Val-CTC Resin

    Fmoc-Gln(Trt)-Val-Pro-Phe-Ser(tBu)-Val-CTC Resin

    H2N-Gln(Trt)-Val-Pro-Phe-Ser(tBu)-Val-CTC Resin

    Fmoc-Asp(OtBu)-Gln(Trt)-Val-Pro-Phe-Ser(tBu)-Val-CTC Resin

    H2N-Asp(OtBu)-Gln(Trt)-Val-Pro-Phe-Ser(tBu)-Val-CTC Resin

    Fmoc-Thr(tBu)-Asp(OtBu)-Gln(Trt)-Val-Pro-Phe-Ser(tBu)-Val-CTC Resin

    H2N-Thr(tBu)-Asp(OtBu)-Gln(Trt)-Val-Pro-Phe-Ser(tBu)-Val-CTC Resin

    Fmoc-Ile-Thr(tBu)-Asp(OtBu)-Gln(Trt)-Val-Pro-Phe-Ser(tBu)-Val-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-Ile-Thr(tBu)-Asp(OtBu)-Gln(Trt)-Val-Pro-Phe-Ser(tBu)-Val-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-Ile-Thr-Asp-Gln-Val-Pro-Phe-Ser-Val-COOH。结构图见产品结构图。

    切割液选择: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

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