Fmoc-Val-ala-PAB

Base Information

• Chemical Name: Fmoc-Val-ala-PAB
• CAS No.: 1394238-91-5
• Molecular Formula: C₃₀H₃₃N₃O₅
• Molecular Weight: 515.609
• Mol file: 1394238-91-5.mol

Synonyms:(9H-fluoren-9-yl)methyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)- 1-oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate

Chemical Property of Fmoc-Val-ala-PAB

Chemical Property:

• Melting Point: 218 °C(dec.)

Purity/Quality:

98% ^*data from raw suppliers

Fmoc-Val-Ala-PAB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Fmoc-Val-Ala-PAB is a cleavable ADC linker. The Val-Ala is effectively cleaved by lysosomal proteolytic enzymes while being highly stable in human plasma, making this a potentent stragy in ADC linker design. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations.
• Uses: Fmoc-Val-Ala-PAB is a building block used in the synthesis of RGD peptidomimetic-paclitaxel conjugates bearing lysosomally cleavable linkers.

Technology Process of Fmoc-Val-ala-PAB

There total 8 articles about Fmoc-Val-ala-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: 100.0%

N-(9-fluorenylmethoxycarbonyl)-L-valyl-L-alanine (150114-97-9) + 4-aminobenzenemethanol (623-04-1) → (9H-fluoren-9-yl)methyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)- 1-oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate (1394238-91-5)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In methanol; dichloromethane; at 20 ℃; for 26h;

Reference yield: 74.59%

(S)-2-amino-N-(4-(hydroxymethyl)phenyl)propionamide (607383-80-2) + Fmoc-Val-OH (68858-20-8) → (9H-fluoren-9-yl)methyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)- 1-oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate (1394238-91-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield:

Fmoc-Val-OH (68858-20-8) → (9H-fluoren-9-yl)methyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)- 1-oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate (1394238-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dicyclohexyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione / tetrahydrofuran / 16 h / 20 °C

1.2: 16 h / 20 °C

2.1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.3390/ijms18091860

upstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-L-valyl-L-alanine

4-aminobenzenemethanol

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

(S)-2-amino-N-(4-(hydroxymethyl)phenyl)propionamide

Downstream raw materials:

H₂N-Val-Ala-PABC-DOXO

EMC-Val-Ala-PABC-DOXO

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