PENTAGASTRIN

Base Information

• Chemical Name: PENTAGASTRIN
• CAS No.: 5534-95-2
• Deprecated CAS: 15686-70-1,5118-28-5,7488-96-2,77055-37-9
• Molecular Formula: C37H49 N7 O9 S
• Molecular Weight: 767.904
• European Community (EC) Number: 226-889-7
• UNII: EF0NX91490
• DSSTox Substance ID: DTXSID3048992
• Nikkaji Number: J3.414B
• Wikipedia: Pentagastrin
• Wikidata: Q423586
• NCI Thesaurus Code: C66340
• Pharos Ligand ID: MCHUK69NZYKL
• Metabolomics Workbench ID: 144384
• ChEMBL ID: CHEMBL1328
• Mol file: 5534-95-2.mol

Synonyms:Alaninamide,N-carboxy-b-alanyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-,N-tert-butyl ester, L- (7CI,8CI);L-Phenylalaninamide,N-[(1,1-dimethylethoxy)carbonyl]-b-alanyl-L-tryptophyl-L-methionyl-L-a-aspartyl-;AY 6608;BOC-b-Ala-Try-Met-Asp-Phe(NH2);ICI 50123;N-(a-Carbamoylphenethyl)-3-[2-[2-[3-(carboxyamino)propionamido]-3-indol-3-ylpropionamido]-4-(methylthio)butyramido]succinamicacid N-tert-butyl ester;N-Carboxy-b-alanyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-L-alaninamideN-tert-butyl ester;N-t-Butyloxycarbonyl-b-alanyl-L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalanineamide;NSC 367746;Pentagastrin;Peptavlon;t-Butoxycarbonyl-b-Ala-Trp-Met-Asp-Phe-NH2;

Chemical Property of PENTAGASTRIN

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 229-230° (dec)
• Refractive Index: 1.604
• Boiling Point: 1196.6°Cat760mmHg
• PKA: 4.19±0.10(Predicted)
• Flash Point: 677.5°C
• PSA: 276.21000
• Density: 1.303g/cm³
• LogP: 4.17500
• Storage Temp.: −20°C
• Solubility.: Practically insoluble in water; soluble in 5M ammonia and in dimethylformamide; slightly soluble in ethanol (96%).
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 22
• Exact Mass: 767.33124734
• Heavy Atom Count: 54
• Complexity: 1310

Purity/Quality:

98%min ^*data from raw suppliers

Gastrin Releasing Peptide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 61-36/38-20/21
• Safety Statements: 53-45-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCSC)C(=O)NC(CC(=O)O)C(=O)NC(CC3=CC=CC=C3)C(=O)N
• Isomeric SMILES: CC(C)(C)OC(=O)NCCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N
• Recent ClinicalTrials: A New Method for Determining Gastric Acid Output Using a Wireless Capsule
• Recent EU Clinical Trials: Calcitonin stimulation: pentagastrin vs. calcium gluconate - potency, feasibility and tolerance in chronic kidney disease.
• Description: Pentagastrin is a synthetic polypeptide and cholecystokinin-2 (CCK2) receptor agonist. It binds selectively to CCK2 receptors in guinea pig brain over CCK1 receptors in rat pancreas (IC50s = 11 and 1,100 nM, respectively). Pentagastrin increases calcium influx and polyphosphoinositide turnover in rat GH3 pituitary cells (EC50s = 23 and 3.9 nM, respectively). It also increases histidine decarboxylase activity in mucous- and endocrine cell-enriched isolated rabbit fundic mucosal cells (EC50 = 2.9 nM). Pentagastrin induces contraction of isolated pig ileum smooth muscle cells in vitro (EC50 = 30 pM). It increases gastric acid and pepsin secretion in conscious cats in vivo (ED50s = 1.29 and 57.3 nmol/kg2 per hour, respectively). Formulations containing pentagastrin have previously been used as a diagnostic aid to evaluate gastric acid secretory function.
• Uses: Pentagastrin is a synthetic polypeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid as the pentagastrin-stimulated calcitonin test. anesthetic (local) diagnostic agent for gastric secretion disorders
• Therapeutic Function: Gastrosecretory hormone

Technology Process of PENTAGASTRIN

There total 19 articles about PENTAGASTRIN 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: 86.0%

L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide hydrochloride (5609-49-4) + Boc-β-Ala-ONB (65785-41-3) → pentagastrin (5534-95-2,77055-37-9,7488-96-2)

Guidance literature:

With 4-methyl-morpholine; for 48h;

Reference yield: 24.0%

→ pentagastrin (5534-95-2,77055-37-9,7488-96-2)

Guidance literature:

Reference yield:

L-Phenylalanine amide (5241-58-7) → pentagastrin (5534-95-2,77055-37-9,7488-96-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) DMF, 15 min, -18 deg C; 2.) 2 h, -10 - -20 deg C; 4 h, room temperature

2: 84 percent / H₂ / Pd black / methanol / 12 h

3: 80 percent / HONB, DCCI / dimethylformamide / 1.) 2 h, -20 deg C; 2.) 3 h, room temperature

4: 98 percent / HCl, CH₃COOH, C₂H₅SH / 0.75 h / Ambient temperature

5: 86 percent / N-methylmorpholine / 48 h

With 4-methyl-morpholine; hydrogenchloride; hydrogen; acetic acid; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide); ethanethiol; isobutyl chloroformate; palladium; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide hydrochloride

Boc-β-Ala-ONB

Boc-βAla-Δ^ZTrp-Met-Asp-Phe-NH2

L-methionine

Downstream raw materials:

Boc-βAla-Δ^ZTrp-Met-Asp-Phe-NH2

Refernces

• 1、 Hammadi, Akli,Lam, Hubert,Gondry, Muriel,Ménez, André,Genet, Roger. "Asymmetric reduction of (Z)-α,β-dehydrotryptophanyl-containing biological peptides with sulfur functionality. Influence of substrate on stereoselectivity". . p. 4473 - 4477. Retrieved 2007/10/03.
• 2、 -. "N-SUBSTITUTED CYCLOALKYL AND POLYCYCLOALKYL ALPHA-SUBSTITUTED TRP-PHE- AND PHENETHYLAMINE DERIVATIVES". . . Retrieved 2008/06/13.