tert-Butyl L-tryptophyl-L-methionyl-L-alpha-aspartyl-3-phenyl-L-alaninamidoformate

Base Information

• Chemical Name: tert-Butyl L-tryptophyl-L-methionyl-L-alpha-aspartyl-3-phenyl-L-alaninamidoformate
• CAS No.: 5235-21-2
• Molecular Formula: C34H44 N6 O8 S
• Molecular Weight: 696.825
• DSSTox Substance ID: DTXSID00966733
• Mol file: 5235-21-2.mol

Synonyms:Boc-CCK-4;Boc-CCK4;Boc-Trp-Met-Asp-Phe-NH2;butyloxycarbonyl-tryptophyl-methionyl-aspartyl-phenylalaninamide

Chemical Property of tert-Butyl L-tryptophyl-L-methionyl-L-alpha-aspartyl-3-phenyl-L-alaninamidoformate

Chemical Property:

• Vapor Pressure: 0.0268mmHg at 25°C
• Boiling Point: 255°C at 760 mmHg
• Flash Point: 108°C
• PSA: 247.11000
• Density: 1.097g/cm³
• LogP: 4.27780
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 19
• Exact Mass: 696.29413356
• Heavy Atom Count: 49
• Complexity: 1160

Purity/Quality:

99% ^*data from raw suppliers

BOC TETRAGASTRIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=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)NC(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

Technology Process of tert-Butyl L-tryptophyl-L-methionyl-L-alpha-aspartyl-3-phenyl-L-alaninamidoformate

There total 11 articles about tert-Butyl L-tryptophyl-L-methionyl-L-alpha-aspartyl-3-phenyl-L-alaninamidoformate 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-Phenylalanine amide (5241-58-7) + Boc-Trp-Met-Asp-OH (123197-15-9) → N-tert-butoxycarbonyl-L-tryptophyl->L-methionyl->L-α-aspartyl->L-phenylalanine amide (5235-21-2)

Guidance literature:

With thermolysin; In methanol; water; for 18h; Ambient temperature; pH 6.0;

DOI:10.1248/cpb.36.4345

Reference yield:

(tert-butyloxycarbonyl)-l-tryptophan p-nitrophenyl ester (15160-31-3) → N-tert-butoxycarbonyl-L-tryptophyl->L-methionyl->L-α-aspartyl->L-phenylalanine amide (5235-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 3 N HCl; 2.) Et₃N / 1.) dioxane, room t, 1 h; 2.) DMF, water, 16 h

2: 86 percent / thermolysin / methanol; H₂O / 18 h / Ambient temperature; effect of the pH

With hydrogenchloride; triethylamine; thermolysin; In methanol; water;

DOI:10.1248/cpb.36.4345

Reference yield:

Boc-Met-Asp-OH (103802-00-2) → N-tert-butoxycarbonyl-L-tryptophyl->L-methionyl->L-α-aspartyl->L-phenylalanine amide (5235-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 3 N HCl; 2.) Et₃N / 1.) dioxane, room t, 1 h; 2.) DMF, water, 16 h

2: 86 percent / thermolysin / methanol; H₂O / 18 h / Ambient temperature; effect of the pH

With hydrogenchloride; triethylamine; thermolysin; In methanol; water;

DOI:10.1248/cpb.36.4345

upstream raw materials:

L-Phenylalanine amide

Boc-Trp-Met-Asp-OH

N^α-tert-Butyloxycarbonyl-L-methionyl-L-aspartyl-L-phenylalanine amide

(tert-butyloxycarbonyl)-l-tryptophan p-nitrophenyl ester

Downstream raw materials:

N-{[4,5-bis-(4-methoxy-phenyl)-2-oxo-oxazol-3-yl]-acetyl}-L-tryptophyl->L-methionyl->L-α-aspartyl->L-phenylalanine amide

H-Trp-Met-Asp-Phe-NH₂*TFA

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

Refernces

• 1、 Sakina,Kawazura,Morihara,Yajima. "Thermolysin-catalyzed synthesis of peptide amides". . p. 4345 - 4354. Retrieved 2007/10/02.
• 2、 -. "α-AMINOACYL CONTAINING NEW PEPTIDES WITH GASTRIN EFFECTS AND A PROCESS FOR THE PREPARATION THEREOF". . . Retrieved 2008/06/13.