GLN-ARG-PRO-ARG-LEU-SER-HIS-LYS-GLY-PRO-MET-PRO-PHE

Base Information

• Chemical Name: GLN-ARG-PRO-ARG-LEU-SER-HIS-LYS-GLY-PRO-MET-PRO-PHE
• CAS No.: 217082-58-1
• Molecular Formula: C69H111N23O16S
• Molecular Weight: 1550.85
• Mol file: 217082-58-1.mol

Synonyms:14: PN:WO2007039184 SEQID: 14 claimed sequence;15: PN: WO2004081198 SEQID: 4 claimedsequence;17: PN: WO2006023893 SEQID: 4 claimed sequence;17: PN: WO2006076736SEQID: 4 claimed sequence;1: PN: WO2009033784 PAGE: 98 claimed protein;2: PN:WO2009033819 PAGE: 103 claimed protein;65-77-Apelin (Mus musculus);65-77-Apelin, prepro-;7: PN: WO2005023863 SEQID: 7 claimed sequence;Apelin-13;

Chemical Property of GLN-ARG-PRO-ARG-LEU-SER-HIS-LYS-GLY-PRO-MET-PRO-PHE

Chemical Property:

• PKA: 3.56±0.10(Predicted)
• PSA: 653.27000
• Density: 1.5 g/cm³
• LogP: 2.10150
• Storage Temp.: −20°C
• Solubility.: Soluble in PBS (pH 7.2) at approximately 10 mg/ml.

Purity/Quality:

98%,99%, ^*data from raw suppliers

Apelin 13 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Apelin-13 trifluoroacetate salt has been used to determine whether apelin promotes progression of diabetic nephropathy (DN) by inducing podocyte dysfunction. It has also been used to examine the effects of apelin on myocardial infarction (MI) injury and underlying mechanisms. The apelin gene encodes a pre-proprotein that is processed to generate bioactive peptides consisting of 36, 17, or 13 amino acids (apelin-36, apelin-17, and apelin-13, respectively). Apelin-13 is the endogenous ligand of the APJ receptor, activating this G protein-coupled receptor with an EC50 value of 0.37 nM (the EC50 values for apelin-17 and apelin-36 are 2.5 and 20 nM, respectively). It acts primarily in the periphery and central nervous system, playing important roles in regulating cardiovascular function, fluid homeostasis, hypertension, and insulin sensitivity. Unlike apelin-36, apelin-13 poorly blocks the entry of human immunodeficiency virus into cells. An endogenous ligand of Apelin Receptor (APLNR/APJ receptor) that plays important roles in regulating fluid homeostasis, cardiovascular function, and insulin sensitivity.

Technology Process of GLN-ARG-PRO-ARG-LEU-SER-HIS-LYS-GLY-PRO-MET-PRO-PHE

There total 2 articles about GLN-ARG-PRO-ARG-LEU-SER-HIS-LYS-GLY-PRO-MET-PRO-PHE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Fmoc-Phe-Wang resin + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Fmoc-L-Gln(Trt)-OH (132327-80-1,200623-62-7) + Fmoc-His(Trt)-OH (109425-51-6) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → Apelin-13 (217082-58-1)

Guidance literature:

Fmoc-Phe-Wang resin; With piperidine; In 1-methyl-pyrrolidin-2-one; Wang resin

Fmoc-Pro-OH; With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide; In 1-methyl-pyrrolidin-2-one; Wang resin

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl); N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Fmoc-L-Gln(Trt)-OH; Fmoc-His(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Further stages;

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + (9-fluorenylmethoxycarbonyl)-L-histidine (116611-64-4) → Apelin-13 (217082-58-1)

Guidance literature:

N-Fmoc L-Phe; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; for 0.5h;

With piperidine; In N,N-dimethyl-formamide;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; Fmoc-Pro-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; (9-fluorenylmethoxycarbonyl)-L-histidine; Fmoc-Lys(pg)-OH; Fmoc-Ser(pg)-OH; Fmoc-Arg(pg)-OH; Fmoc-Gln(pg)-OH; Further stages;

DOI:10.1016/j.bmc.2014.04.001

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Leu-OH

Fmoc-Pro-OH

N-Fmoc L-Phe

Refernces

• 1、 Zhang, Yanyan,Maitra, Rangan,Harris, Danni L.,Dhungana, Suraj,Snyder, Rodney,Runyon, Scott P.. "Identifying structural determinants of potency for analogs of apelin-13: Integration of C-terminal truncation with structure-activity". . p. 2992 - 2997. Retrieved 2014/05/20.