FMoc-Val-Cit-PAB

Base Information

• Chemical Name: FMoc-Val-Cit-PAB
• CAS No.: 159858-22-7
• Molecular Formula: C33H39N5O6
• Molecular Weight: 601.703
• Mol file: 159858-22-7.mol

Synonyms:FMoc-Val-Cit-PAB

Chemical Property of FMoc-Val-Cit-PAB

Chemical Property:

• Melting Point: 204 °C(dec.)
• Boiling Point: 914.2±65.0 °C(Predicted)
• PKA: 10.63±0.46(Predicted)
• PSA: 171.88000
• Density: 1.276±0.06 g/cm3(Predicted)
• LogP: 5.56000
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-Val-Cit-PAB-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Fmoc-Val-Cit-PAB is a commonly used bridge for a degradable antibody-conjugated drug (ADC).
• Description: Fmoc-Val-Cit-PAB-OH is a cleavable ADC linker. The Val-Cit will specifically be cleaved by Cathepsin B. As this enzyme is only present in the lysosome, the ADC payload will be released only in the cell. Fmoc can be deprotected under basic condition.

Technology Process of FMoc-Val-Cit-PAB

There total 17 articles about FMoc-Val-Cit-PAB 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: 98.0%

(S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid (159858-21-6) + 4-aminobenzenemethanol (623-04-1) → (9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate (159858-22-7)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In methanol; dichloromethane; at 20 ℃; for 18.0833h;

Reference yield: 94.0%

→ (9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate (159858-22-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 5h;

Reference yield: 78.0%

(S)-2-amino-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide (1037794-22-1) + 2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate (130878-68-1) → (9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate (159858-22-7)

Guidance literature:

In N,N-dimethyl-formamide; at 30 ℃; for 2h;

DOI:10.1021/acs.jmedchem.7b01430

upstream raw materials:

(S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid

4-aminobenzenemethanol

Fmoc-Val-OH

2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

Downstream raw materials:

(9H-fluoren-9-yl)methyl ((S)-3-methyl-1-(((S)-1-((4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-1-oxobutan-2-yl)carbamate