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Inhibitor of dipeptidylpeptidase IV (DPP IV).

Peptide H-APG-OH is a Research Peptide with significant interest within the field academic and medical research. Recent citations using H-APG-OH include the following: Binding of a membrane proteoglycan from Klebsiella pneumoniae and its derivatives to human leukocytes Z Hmama, G Normier, E Kouassi, M Flacher, H Binz - Immunobiology, 1992 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0171298511802494 Role of acyl residues in polyclonal murine B cell activation by acylpoly (1, 3) galactosides from Klebsiella pneumoniae. Z Hmama, G Lina, G Normier, H Binz - Journal of immunology , 1993 - journals.aai.orghttps://journals.aai.org/jimmunol/article-abstract/151/10/5440/27696 Antibacterial effect of autologous platelet-rich gel derived from health volunteers in vitro Y Yang, H Liu, G Liu, X Ran - Zhongguo xiu fu chong jian wai ke za , 2010 - europepmc.orghttps://europepmc.org/article/med/20540263 The targeted development of collagen-active peptides based on composite enzyme hydrolysis: a study on the structure-activity relationship X Hu, Y Yang, C Chang, J Li, Y Su, L Gu - Food & Function, 2024 - pubs.rsc.orghttps://pubs.rsc.org/en/content/articlehtml/2023/fo/d3fo04455f In Vitro and In Silico Studies on Angiotensin I-Converting Enzyme Inhibitory Peptides Found in Hydrophobic Domains of Porcine Elastin T Hatakenaka, T Kato, K Okamoto - Molecules, 2023 - mdpi.comhttps://www.mdpi.com/1420-3049/28/8/3337 Isolation and charaterization of bioactive peptides from hwangtae (yellowish dried alaska pollack) protein hydrolysate SS Cho, HK Lee, CY Yu, MJ Kim - Nutrition and Food , 2008 - koreascience.krhttps://koreascience.kr/article/JAKO200828955288452.page Use of a Poly-γ-Glutamic Acid-Derived Amphipathic Polypeptide for the Reconstitution of Membrane Proteins. SG Han , SB Choi, NH Kim, S Kang - Bulletin of the Korean , 2020 - search.ebscohost.comhttps://search.ebscohost.com/login.aspx?direct=true&profile=ehost&scope=site&authtype=crawler&jrnl=02532964&asa=N&AN=144222090&h=jfCRFIHuB0TCI6xz%2BxRL0KToYki9Nj3zOPRGrV%2BOxDx5SC6SUXwtcW91nLoxGcbreFlvICVuu5MSQKFG1TQxLw%3D%3D&crl=c An amphipathic polypeptide derived from poly-γ-glutamic acid for the stabilization of membrane proteins SG Han , JH Na , WK Lee , D Park, J Oh - Protein , 2014 - Wiley Online Libraryhttps://onlinelibrary.wiley.com/doi/abs/10.1002/pro.2575 Fluorous Peptide Nucleic Acids: PNA Analogues with Fluorine in Backbone (γ-CF2-apg-PNA) Enhance Cellular Uptake S Ellipilli , KN Ganesh - The Journal of organic chemistry, 2015 - ACS Publicationshttps://pubs.acs.org/doi/abs/10.1021/acs.joc.5b01614 Cationic Antimicrobial Peptides have Reduced Binding to MprF-Modified Membranes PW Simcock, MS Sansom , PJ Stansfeld , M Bublitz - Biophysical , 2020 - cell.comhttps://www.cell.com/biophysj/pdf/S0006-3495(19)32331-8.pdf PGAIPG, a repeated hexapeptide of bovine tropoelastin, is a ligand for the 67-kDa bovine elastin receptor LE Grosso, M Scott - Matrix, 1993 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0934883211800740 Single-Crystal Studies of Peptide Prolyl and Glycyl 15N Shielding Tensors KW Waddell, EY Chekmenev - Journal of the American , 2005 - ACS Publicationshttps://pubs.acs.org/doi/abs/10.1021/ja044204h Conformational change of the triple-helical structure. II. Conformation of (Pro-Pro-Gly)n and (Pro-Pro-Gly)n(Ala-Pro-Gly)m(Pro-Pro-Gly)n in an aqueous K Sutoh, H Noda - Biopolymers: Original Research on , 1974 - Wiley Online Libraryhttps://onlinelibrary.wiley.com/doi/abs/10.1002/bip.1974.360131118 Apg-2 has a chaperone-like activity similar to Hsp110 and is overexpressed in hepatocellular carcinomas K Gotoh, K Nonoguchi, H Higashitsuji, Y Kaneko - FEBS letters, 2004 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0014579304000341 Effects of alkyl polyglycoside (APG) on Bombyx mori silk degumming and the mechanical properties of silk fibroin fibre F Wang, YQ Zhang - Materials Science and Engineering: C, 2017 - Elsevierhttps://www.sciencedirect.com/science/article/pii/S0928493117304629 Aminopropyl glass and its p-phenylene diisothiocyanate derivative, a new support in solid-phase Edman degradation of peptides and proteins E Wachter, W Machleidt, H Hofner, J Otto - FEBS letters, 1973 - core.ac.ukhttps://core.ac.uk/download/pdf/81200622.pdf The sequence of an atriopeptigen: a precursor of the bioactive atrial peptides DM Gelher, MG Currie , NR Siegel, KF Fok - Biochemical and , 1984 - Elsevierhttps://www.sciencedirect.com/science/article/pii/0006291X84907496 Arginine selective reagents for ligation to peptides and proteins DA Thompson , R Ng, PE Dawson - Journal of Peptide Science, 2016 - Wiley Online Libraryhttps://onlinelibrary.wiley.com/doi/abs/10.1002/psc.2867 Molecular architecture of secretin receptors: The specific covalent labelling of a 51 kDa peptide after cross-linking of 125Iiodo-secretin to intact rat pancreatic acini D Gossen, P Poloczek, M Svoboda , J Christophe - FEBS letters, 1989 - Wiley Online Libraryhttps://febs.onlinelibrary.wiley.com/doi/abs/10.1016/0014-5793(89)80130-9 Evaluation of alkyl polyglucoside as an alternative surfactant in the preparation of peptide-loaded nanoparticles AR Patel , S Kulkarni, TD Nandekar - Journal of , 2008 - Taylor & Francishttps://www.tandfonline.com/doi/abs/10.1080/02652040802075526 Synthesis and self-assembly of amphiphilic precision glycomacromolecules A Banger, J Sindram, M Otten, J Kania, D Wilms - Polymer , 2021 - pubs.rsc.orghttps://pubs.rsc.org/en/content/articlehtml/2021/py/d1py00422k

多肽H2N-Ala-Pro-Gly-COOH的合成步骤：

1、合成CTC树脂：称取2.02g CTC Resin（如初始取代度约为0.57mmol/g）和1.38mmol Fmoc-Gly-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3.45mmol 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-Gly-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-Gly-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3.45mmol Fmoc-Pro-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6.91mmol DIPEA，3.28mmol 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-Pro-Gly-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-Pro-Gly-CTC Resin

Fmoc-Ala-Pro-Gly-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-Pro-Gly-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-Pro-Gly-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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