6-Maleimidocaproic acid-PFP ester

Base Information

• Chemical Name: 6-Maleimidocaproic acid-PFP ester
• CAS No.: 692739-25-6
• Molecular Formula: C16H12F5NO4
• Molecular Weight: 377.268
• Mol file: 692739-25-6.mol

Synonyms:6-maleimidohexanoic acid pentafluorophenyl ester;6-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-hexanoic acid pentafluorophenyl ester;pentafluorophenyl 6-maleimidohexanoate;

Chemical Property of 6-Maleimidocaproic acid-PFP ester

Chemical Property:

• PSA: 63.68000
• LogP: 2.71080

Purity/Quality:

97% ^*data from raw suppliers

6-Maleimidocaproicacidpentafluorophenylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 6-Maleimidocaproic acid PFP ester contains a maleimide and PFP ester end group. Maleimides react with thiol groups within the pH range of 6.5 to 7.5 and form stable thioester bonds. PFP is an activated ester which can react with amine groups to form stable amide bonds.

Technology Process of 6-Maleimidocaproic acid-PFP ester

There total 2 articles about 6-Maleimidocaproic acid-PFP ester 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: 100.0%

maleic anhydride (108-31-6) + 6-aminohexanoic acid (60-32-2,93208-38-9) → pentafluorophenyl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate (692739-25-6)

Guidance literature:

With acetic acid; at 120 ℃;

Reference yield: 93.0%

2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (55750-53-3) + 2,3,4,5,6-pentafluorophenol (771-61-9) → pentafluorophenyl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate (692739-25-6)

Guidance literature:

With diisopropyl-carbodiimide; In ethyl acetate; for 4h; cooling;

DOI:10.1248/cpb.55.685

Reference yield: 95.0%

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide (159857-79-1) + pentafluorophenyl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate (692739-25-6) → 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide (159857-80-4)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃;

upstream raw materials:

2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid

2,3,4,5,6-pentafluorophenol

maleic anhydride

6-aminohexanoic acid

Downstream raw materials:

6-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexanoylamino]-hexanoic acid pentafluorophenyl ester

pentafluorophenyl 6-(6-(6-maleimidohexanamido)hexanamido)hexanoate

6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide

N-((S)-1-(((S)-1-((4-(chloromethyl)phenyl)amino)-1-oxo-5-ureidopentan- 2-yl)amino)-3-methyl-1-oxobutan-2-yl)-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamide