L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]-

Base Information

• Chemical Name: L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]-
• CAS No.: 159857-81-5
• Molecular Formula: C35H43N7O11
• Molecular Weight: 737.767
• Mol file: 159857-81-5.mol

Synonyms:maleimidocaproyl-val-Cit-PAB-OCOpNP;N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide;N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N-carbamoyl-N-[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide;4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl (4-nitrophenyl)carbonate;N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N-[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide;maleimido-caproyl-valine-citrulline-para-aminobenzyl-4-nitrophenylcarbonate;MC-VAL-CIT-PAB-PNB;Mc-Val-Cit-PABC-PNP;

Chemical Property of L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]-

Chemical Property:

• Boiling Point: 1034.5±65.0 °C(Predicted)
• PKA: 13.24±0.70(Predicted)
• PSA: 261.15000
• Density: 1.338±0.06 g/cm3(Predicted)
• LogP: 5.21550
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

mc-Val-Cit-PABC-PNP 80% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Mc-Val-Cit-PABC-PNP is a peptide linker molecule used in the synthesis of antibody-drug conjugates (ADCs). It contains a maleimidocaproyl (Mc) group that can be conjugated to an antibody and a p-nitrophenol (PNP) group that allows the peptide to be linked to anticancer compounds, such as doxorubicin or monomethyl auristatin E (MMAE; ). ADCs target specific cell populations to induce a selective response, such as cell death in cancer cells.
• Uses: Mc-Val-Cit-PABC-PNP is a cathepsin cleavable ADC linker used in the synthesis of antibody-drug conjugates.

Technology Process of L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]-

There total 19 articles about L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]- 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: 95.0%

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) + bis-(p-nitrophenyl) carbonate (5070-13-3) → N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide (159857-81-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃;

Reference yield: 7.0%

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) + 4-Nitrophenyl chloroformate (7693-46-1) → N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide (159857-81-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

Reference yield:

6-maleimidohexanoic acid N-hydroxylsuccinimide ester (55750-63-5) → N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide (159857-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 12 h / 20 °C / Inert atmosphere

With pyridine; In 1-methyl-pyrrolidin-2-one; dichloromethane;

upstream 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

bis-(p-nitrophenyl) carbonate

N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N⁵-carbamoyl-L-ornithine

4-aminobenzenemethanol

Downstream raw materials:

maleimidocaproyl-Val-Cit-PAB-MeVal-Val-Dil-Dap-2-chloro-Phe-OH

maleimidocaproyl-val-Cit-p-aminobenzoyl-NMeVal-Val-Dil-Dap-phosphonophenylalanine

maleimidocaproyl-Val-Cit-p-aminobenzoyl-NMeVal-Val-Dil-Dap-phosphonophenylalanine

MC-Val-Cit-PAB-MeVal-Val-Dil-ODMB

Refernces

• 1、 Li, Zhanzhan,Teng, Da,Mao, Ruoyu,Wang, Xiao,Hao, Ya,Wang, Xiumin,Wang, Jianhua. "Improved Antibacterial Activity of the Marine Peptide N6 against Intracellular Salmonella Typhimurium by Conjugating with the Cell-Penetrating Peptide Tat11 via a Cleavable Linker". . p. 7991 - 8000. Retrieved 2018.
• 2、 -. "DRUG ANTIBODY CONJUGATES". Page/Page column 122; 124. . Retrieved 2021/10/30.
• 3、 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.