FMoc-Val-Cit-PAB Chemical Properties

Melting point:

204 °C(dec.)

Boiling point:

914.2±65.0 °C(Predicted)

Density 

1.276±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

powder to crystal

pka

10.63±0.46(Predicted)

color 

White to Almost white

InChIKey

BJFFTMRUMPZMSZ-VMPREFPWSA-N

SMILES

C(N)(=O)[C@H](CCCNC(N)=O)N(C(=O)[C@H](C(C)C)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)C1=CC=C(CO)C=C1

CAS DataBase Reference

159858-22-7

Safety Information

HS Code 

2924.29.7790

FMoc-Val-Cit-PAB Usage And Synthesis

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.

Uses

Fmoc-Val-Cit-PAB is a cleavable antibody-conjugated active molecule (ADC) commonly used linker.

Synthesis

The general procedure for the synthesis of the target compound (CAS:159858-22-7) from (S)-2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanoylamino) and p-aminobenzenemethanol (PABOH) was carried out as follows: 60 ml of dichloromethane (DCM) mixed with methanol (MeOH) in the ratio of 2:1, by volume of the Solvent was added to the reaction flask, followed by 4.2 mmol Fmoc-vc2g and 1.04 g (2 eq.) of PABOH. after stirring until complete dissolution, 2.0 g (2 eq.) of EEDQ was added. the reaction system was protected from light at room temperature, and the reaction was continuously stirred for 2.0 days. After completion of the reaction, the reaction mixture was concentrated under reduced pressure at 40 °C to give a white solid. The white solid was collected, 100 ml of methyl tert-butyl ether (MTBE) was added, stirred and filtered, and the filter cake was washed with methyl tert-butyl ether. The resulting white solid was dried under reduced pressure at 40 °C to give 2.2 g of the target product in about 88% yield.

IC 50

Protease Cleavable Linker; Cleavable Linker

References

[1] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[2] Patent: CN107789630, 2018, A. Location in patent: Paragraph 0073; 0074; 0075
[3] Patent: WO2017/66668, 2017, A1. Location in patent: Paragraph 000187-000189
[4] Journal of Controlled Release, 2012, vol. 160, # 3, p. 618 - 629
[5] Patent: KR2017/41562, 2017, A. Location in patent: Paragraph 0431-0432

FMoc-Val-Cit-PAB(159858-22-7)Related Product Information

• FMoc-Val-Cit-PAB-PNP
• Val-cit-PAB-OH
• pyrene-2,7-diyldiboronic acid
• Fmoc-Val-Cit-OH
• MC-Val-Cit-PAB
• N-[(9H-Fluoren-9-ylmethoxy)carbonyl]glycylglycylglycylglycine
• Fmoc-Val-Ala-OH
• H-GLY-GLY-PHE-OH
• Fmoc-Val-Ala-PAB-OH
• Fomc-Gly-Gly-Phe-Gly-OH