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The lactokinin ALPMHIR is an angiotensin-converting enzyme (ACE) inhibitory peptide, which corresponds to a sequence released by tryptic digestion from the milk protein β-lactoglobulin. It might be useful in the treatment of hypertension although its ACE inhibitory activity is about a 100 times lower than that of the antihypertensive drug captopril.

Peptide H-ALPMHIR-OH is a Research Peptide with significant interest within the field academic and medical research. Recent citations using H-ALPMHIR-OH include the following: Separation and identification of ACE inhibitory peptides from defatted walnut meal Y Chen, J Li, N Dong, Y Zhang, X Lu, Y Hao - European Food Research , 2020 - Springerhttps://link.springer.com/article/10.1007/s00217-020-03553-5 Novel ACE inhibitory peptides derived from whey protein hydrolysates: Identification and molecular docking analysis X Li, C Feng, H Hong , Y Zhang , Z Luo, Q Wang, Y Luo - Food Bioscience, 2022 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S2212429222001961 Influence of the lactokinin Ala-Leu-Pro-Met-His-Ile-Arg (ALPMHIR) on the release of endothelin-1 by endothelial cells W Maes, J Van Camp, V Vermeirssen , M Hemeryck - Regulatory peptides, 2004 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0167011503002970 Novel whey-derived peptides with inhibitory effect against angiotensin-converting enzyme: In vitro effect and stability to gastrointestinal enzymes T Tavares, M del Mar Contreras , M Amorim , M Pintado - Peptides, 2011 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S019697811100074X A novel LC-MS application to investigate oxidation of peptides isolated from beta-lactoglobulin T Koivumaeki, G GuÃ\x8cË\x86rbuÃ\x8cË\x86z, M Poutanen - Journal of agricultural , 2012 - ACS Publicationshttps://pubs.acs.org/doi/abs/10.1021/jf300360c Seventeen novel angiotensin converting enzyme (ACE) inhibitory peptides from the protein hydrolysate of Mytilus edulis: Isolation, identification, molecular docking SK Suo, YQ Zhao, YM Wang, XY Pan, CF Chi - Food & Function, 2022 - pubs.rsc.orghttps://pubs.rsc.org/en/content/articlehtml/2022/fo/d2fo00275b In silico analysis and molecular docking study of angiotensin I-converting enzyme inhibitory peptides from smooth-hound viscera protein hydrolysates fractionated by O Abdelhedi, R Nasri , L Mora, M Jridi , F Toldra , M Nasri - Food chemistry, 2018 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S030881461731097X A flounder fish peptide shows anti-hypertensive effects by suppressing the renin-angiotensin-aldosterone system and Endothelin-1 M Rahmdel, SM Cho, YJ Jeon - Protein and Peptide , 2021 - ingentaconnect.comhttps://www.ingentaconnect.com/content/ben/ppl/2021/00000028/00000007/art00012 Formation of peptide layers and adsorption mechanisms on a negatively charged cation-exchange membrane M Persico, S Mikhaylin , A Doyen , L Firdaous - Journal of colloid and , 2017 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0021979717309347 Fouling prevention of peptides from a tryptic whey hydrolysate during electromembrane processes by use of monovalent ion permselective membranes M Persico, L Bazinet - Journal of membrane science, 2018 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0376738817327916 Semi-Industrial Production of a DPP-IV and ACE Inhibitory Peptide Fraction from Whey Protein Concentrate Hydrolysate by Electrodialysis with Ultrafiltration M Faucher, TR Geoffroy , J Thibodeau, S Gaaloul - Membranes, 2022 - mdpi.comhttps://www.mdpi.com/2077-0375/12/4/409 Reactivity of peptides within the food matrix JP Kamdem , A Tsopmo - Journal of food Biochemistry, 2019 - Wiley Online Libraryhttps://onlinelibrary.wiley.com/doi/abs/10.1111/jfbc.12489 Preparation of ingredients containing an ACE-inhibitory peptide by tryptic hydrolysis of whey protein concentrates I Ferreira, O Pinho, MV Mota, P Tavares - International Dairy , 2007 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S095869460600166X In Silico Strategies to Predict Anti-aging Features of Whey Peptides GR Rama, LF Saraiva Macedo Timmers - Molecular , 2023 - Springerhttps://link.springer.com/article/10.1007/s12033-023-00887-9 LC-MS investigations on interactions between isolated beta-lactoglobulin peptides and lipid oxidation product malondialdehyde G Gurbuz, M Heinonen - Food Chemistry, 2015 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0308814614018925 Production and membrane fractionation of bioactive peptides from a whey protein concentrate F Arrutia , R Rubio, FA Riera - Journal of Food Engineering, 2016 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0260877416300863 Side Chain Cleavage in TEMPO-assisted Free Radical Initiated Peptide Sequencing (FRIPS): Amino Acid Composition Information# CS Lee, I Jang, S Hwangbo, B Moon - Bulletin of the Korean , 2015 - Wiley Online Libraryhttps://onlinelibrary.wiley.com/doi/abs/10.1002/bkcs.10150 Protein-Phenolic Interaction of Tryptic Digests of beta-Lactoglobulin and Cloudberry Ellagitannin B Wang, T Koivumaki, P Kylli, M Heinonen - Journal of agricultural , 2014 - ACS Publicationshttps://pubs.acs.org/doi/abs/10.1021/jf501190x Investigation of beta-lactoglobulin derived bioactive peptides against SARS-CoV-2 (COVID-19): In silico analysis B acaâ\x80¡akÃ\x84±r , B Okuyan, G Ã\x85ÅŸener , T Tunali-Akbay - European Journal of , 2021 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0014299920308736 Studies on the molecular recognition between bioactive peptides and angiotensin-converting enzyme AS Pina , ACA Roque - Journal of Molecular Recognition: An , 2009 - Wiley Online Libraryhttps://onlinelibrary.wiley.com/doi/abs/10.1002/jmr.905 Discordance between in silico & in vitro analyses of ACE inhibitory & antioxidative peptides from mixed milk tryptic whey protein hydrolysate A Chatterjee, SK Kanawjia, Y Khetra , P Saini - Journal of food science and , 2015 - Springerhttps://link.springer.com/article/10.1007/s13197-014-1669-z

多肽H2N-Ala-Leu-Pro-Met-His-Ile-Arg-COOH的合成步骤：

1、合成CTC树脂：称取2.17g CTC Resin（如初始取代度约为0.64mmol/g）和1.67mmol Fmoc-Arg(Pbf)-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4.17mmol 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-Arg(Pbf)-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-Arg(Pbf)-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4.17mmol 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8.33mmol DIPEA，3.96mmol 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-Arg(Pbf)-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-Arg(Pbf)-CTC Resin

Fmoc-His(Trt)-Ile-Arg(Pbf)-CTC Resin

H2N-His(Trt)-Ile-Arg(Pbf)-CTC Resin

Fmoc-Met-His(Trt)-Ile-Arg(Pbf)-CTC Resin

H2N-Met-His(Trt)-Ile-Arg(Pbf)-CTC Resin

Fmoc-Pro-Met-His(Trt)-Ile-Arg(Pbf)-CTC Resin

H2N-Pro-Met-His(Trt)-Ile-Arg(Pbf)-CTC Resin

Fmoc-Leu-Pro-Met-His(Trt)-Ile-Arg(Pbf)-CTC Resin

H2N-Leu-Pro-Met-His(Trt)-Ile-Arg(Pbf)-CTC Resin

Fmoc-Ala-Leu-Pro-Met-His(Trt)-Ile-Arg(Pbf)-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-Ala-Leu-Pro-Met-His(Trt)-Ile-Arg(Pbf)-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-Ala-Leu-Pro-Met-His-Ile-Arg-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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