Val-cit-PAB-OH

Base Information

• Chemical Name: Val-cit-PAB-OH
• CAS No.: 159857-79-1
• Molecular Formula: C18H29N5O4
• Molecular Weight: 379.459
• Mol file: 159857-79-1.mol

Synonyms:Val-cit-PAB-OH;L-Valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide;(S)-2-((R)-2-amino-3-methylbutanamido)-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide

Chemical Property of Val-cit-PAB-OH

Chemical Property:

• Melting Point: 168 °C(dec.)
• Boiling Point: 715.0±60.0 °C(Predicted)
• PKA: 13.75±0.46(Predicted)
• PSA: 159.57000
• Density: 1.243±0.06 g/cm3(Predicted)
• LogP: 2.28940
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99% ^*data from raw suppliers

Val-cit-PAB-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Val-Cit-PAB-OH is a peptide cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). The Val-Cit will specifically be cleaved by Cathepsin B.
• Uses: Val-cit-PAB-OH acts as a reagent in the preparation of cell-penetrating peptidic GRP78 ligand for tumor cell-specific prodrug therapy, preparation of monomethylvaline derivative conjugates with ligands and antibodies for cancer treatment.

Technology Process of Val-cit-PAB-OH

There total 28 articles about Val-cit-PAB-OH 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: 93.0%

(S)-(9H-fluoren-9-yl)methyl (1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate (870487-04-0) + Fmoc-Val-OPfp (86060-87-9) → (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide (159857-79-1)

Guidance literature:

(S)-(9H-fluoren-9-yl)methyl (1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate; With piperidine; In N,N-dimethyl-formamide; at 23 ℃; for 3h;

Fmoc-Val-OPfp; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 23 ℃; for 24h;

With piperidine; In N,N-dimethyl-formamide; at 23 ℃; for 1h;

Reference yield:

tert-butyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentane-2-yl)amino)-3-methyl-1-oxobutane-2-yl)carbamate (870487-09-5) → (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide (159857-79-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 3 h / 20 °C

2: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C

With water; sodium hydroxide; In 1,4-dioxane; dichloromethane;

Reference yield:

4-((S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanamido)benzyl 2,2,2-trifluoroacetate → (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide (159857-79-1)

Guidance literature:

With water; sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 3h;

upstream raw materials:

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

Fmoc-Val-OH

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

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

Downstream raw materials:

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

C₂₉H₄₂N₆O₁₁S₂

C₃₆H₄₅N₇O₁₅S₂

4-((R)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl ((2S)-1-(((2S)-1-(((4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate

Refernces

• 1、 Xiao, Dian,Luo, Longlong,Li, Jiaguo,Wang, Zhihong,Liu, Lianqi,Xie, Fei,Feng, Jiannan,Zhou, Xinbo. "Development of bifunctional anti-PD-L1 antibody MMAE conjugate with cytotoxicity and immunostimulation". . . Retrieved 2021/09/27.
• 2、 -. "PROTEIN-ANTIVIRAL COMPOUND CONJUGATES". . . Retrieved 2021/07/31.