PYR-ARG-PRO-ARG-LEU-SER-HIS-LYS-GLY-PRO-MET-PRO-PHE-OH

Base Information

• Chemical Name: PYR-ARG-PRO-ARG-LEU-SER-HIS-LYS-GLY-PRO-MET-PRO-PHE-OH
• CAS No.: 217082-60-5
• Molecular Formula: C₆₉H₁₀₈N₂₂O₁₆S
• Molecular Weight: 1533.82
• Mol file: 217082-60-5.mol

Synonyms:(Pyr1)apelin-13;(pGlu1)apelin-13; Pyr-apelin-13

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

Chemical Property:

• PKA: 3.56±0.10(Predicted)
• PSA: 613.26000
• Density: 1.51±0.1 g/cm3(Predicted)
• LogP: 1.71550
• Storage Temp.: -15°C

Purity/Quality:

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

[Pyr1]-Apelin-13 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 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 an endogenous ligand of the APJ receptor, activating this G protein-coupled receptor with an EC50 value of 0.37 nM. (Glp1)-Apelin-13 is a pyroglutamylated form of apelin-13, in that the N-terminal glutamine residue is cyclized to pyroglutamic acid. Like apelin-13, this compound is a potent APJ receptor agonist (EC50 = 0.30 nM). (Glp1)-Apelin-13 is the major apelin isoform in the plasma of healthy human subjects. It can have vasoconstrictor and antipyretic effects in vitro and in vivo.

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

There total 2 articles about PYR-ARG-PRO-ARG-LEU-SER-HIS-LYS-GLY-PRO-MET-PRO-PHE-OH 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-His(Trt)-OH (109425-51-6) + L-Pyroglutamic acid (98-79-3) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → pyr-1-apelin-13 (217082-60-5)

Guidance literature:

Fmoc-Phe-Wang resin; With piperidine; In N,N-dimethyl-formamide; Wang resin

Fmoc-Pro-OH; With 4-methyl-morpholine; O?(6?chlorobezotriazol?1?yl)?N,N,N,N?tetramethyluronium hexafluorophosphate; In N,N-dimethyl-formamide; for 0.5h; Wang resin

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

DOI:10.1016/j.ab.2018.12.022

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) + L-Pyroglutamic acid (98-79-3) → pyr-1-apelin-13 (217082-60-5)

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; L-Pyroglutamic acid; Fmoc-Lys(pg)-OH; Fmoc-Ser(pg)-OH; Fmoc-Arg(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.