ChemicalBook > CAS DataBase List > FMoc-Val-Cit-PAB-PNP

FMoc-Val-Cit-PAB-PNP

Product Name: FMoc-Val-Cit-PAB-PNP
CAS No.: 863971-53-3
Chemical Name: FMoc-Val-Cit-PAB-PNP
Synonyms: 4-[[(2S)-1-amino-5-(carbamoylamino)-1-oxopentan-2-yl]-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]phenyl]methyl (4-nitrophenyl) carbonate;(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;Moc-Val-Cit-PAB-PNP;Fmoc-Val-Cit-PAB-PN;FMoc-Val-Cit-PAB-PNP;Fmoc-Val-Cit-PABC-PNP;Fmoc-Val-Cit-PAB-PNP-OH;Fmoc-Val-Cit-PAB-PNP, >95%;863971-53-3 FMoc-Val-Cit-PAB-PNP 1g;FMOC-VAL-CIT-PAB-PNP (9-FLUORENYLMETHYLOXYCARBONYL-VALYL-CITRULLYL-(4-AMINOBENZYL)-(4-NITROPHENYL)CARBONATE)
CBNumber: CB92730904
Molecular Formula: C40H42N6O10
Formula Weight: 766.8
MOL File: 863971-53-3.mol

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FMoc-Val-Cit-PAB-PNP Property

Melting point:: 189 °C(dec.)
Boiling point:: 1024.0±65.0 °C(Predicted)
Density: 1.335±0.06 g/cm3(Predicted)
storage temp.: 2-8°C(protect from light)
form: powder to crystal
pka: 10.63±0.46(Predicted)
color: White to Light yellow
Sequence: Fmoc-Val-Cit-PAB-PNP
InChIKey: RFBGUFDKKIFDDF-PXLJZGITSA-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(COC(OC2=CC=C([N+]([O-])=O)C=C2)=O)C=C1

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Safety

HS Code: 2924.29.7790

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning
Hazard statements: H227Combustible liquid
Precautionary statements: P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

TCI Chemical

Product number: F1114
Product name: Fmoc-Val-Cit-PAB-PNP
Packaging: 100MG
Price: $182
Updated: 2025/07/31

TCI Chemical

Product number: F1114
Product name: Fmoc-Val-Cit-PAB-PNP
Packaging: 500MG
Price: $724
Updated: 2025/07/31

Iris Biotech GmbH

Product number: ADC1000
Product name: Fmoc-Val-Cit-PAB-PNP
Packaging: 100mg
Price: $168.75
Updated: 2021/12/16

ChemScene

Product number: CS-5172
Product name: Fmoc-Val-Cit-PAB-PNP
Purity: 95.87%
Packaging: 100mg
Price: $170
Updated: 2021/12/16

BroadPharm

Product number: BP-22309
Product name: Fmoc-Val-Cit-PAB-PNP
Purity: 95%
Packaging: 100mg
Price: $255
Updated: 2021/12/16

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FMoc-Val-Cit-PAB-PNP Chemical Properties,Usage,Production

Description

Fmoc-Val-Cit-PAB-PNP is a a cleavable ADC linker used in antibody drug conjugate. The Val-Cit linker was designed to be cleaved by cathepsin B. PNP group is a good leaving group when reacting with amine bearing payload.

Uses

Fmoc-Val-Cit-PAB-PNP is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). Fmoc-Val-Cit-PAB-PNP has superior plasma stability comparable to that of non-cleavable linkers[1][2][3].

Biological Activity

Fmoc-Val-Cit-PAB-PNP is a cleavable ADC linker that can be used to synthesize antibody drug conjugates (ADCs).

Synthesis

5070-13-3

159858-22-7

863971-53-3

General procedure for the synthesis of compound (CAS:863971-53-3) from bis(4-nitrophenyl) carbonate and compound (CAS:159858-22-7): under nitrogen protection, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-carbamoyl-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide ( 1.3 g, 2.16 mmol, prepared as reported in EP0624377A2) was dissolved in 6 mL of anhydrous DMF with bis(4-nitrophenyl) carbonate (1.32 g, 4.34 mmol). After addition of DIPEA (0.75 mL, 4.35 mmol), the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, diethyl ether (120 mL) was added to precipitate the product, and the precipitate was collected by filtration, washed with diethyl ether, and dried under vacuum to afford N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-carbamoyl-N-[4-({{[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide (1.47 g, yield 89%). ESI MS: m/z 767 (MH+). 1H NMR (400MHz, DMSO-d6) δ 0.86 (d, J=6.7Hz, 3H), 0.88 (d, J=6.7Hz, 3H), 1.30-1.52 (m, 2H), 1.60 (m, 1H), 1.69 (m, 1H), 1.99 (m, 1H ), 2.90-3.10 (m, 2H), 3.93 (dd, J=8.9,7.0Hz, 1H), 4.14-4.34 (m, 3H), 4.42 (m, 1H), 5.24 (s, 2H), 5.39 (s, 2H), 5.97 (t, J=5.5Hz, 1H), 7.32 (m, 2H), 7.42 (m, 5H ), 7.55 (m, 2H), 7.65 (d, J=8.4Hz, 2H), 7.74 (t, J=7.9Hz, 2H), 7.88 (d, J=7.6Hz, 2H), 8.12 (d, J=7.4Hz, 1H), 8.31 (m, 2H), 10.12 (s, 1H).

in vivo

Fmoc-Val-Cit-PAB-PNP linker stabilization in the mouse is an essential prerequisite for designing successful efficacy and safety studies in rodents during preclinical stages of ADC programs^[3].
Conjugation site plays an important role in determining VC-PABC linker stability in mouse plasma, and that the stability of the linker positively correlates with ADC cytotoxic potency both in vitro and in vivo^[3].

IC 50

Protease Cleavable Linker; Cleavable Linker

References

[1] Dubowchik GM, et al. Cathepsin B-labile dipeptide linkers for lysosomal release of doxorubicin from internalizing immunoconjugates: model studies of enzymatic drug release and antigen-specific in vitro anticancer activity. Bioconjug Chem. 2002 Jul-Aug;13(4):855-69. DOI:10.1021/bc025536j
[2] Yoneda Y, et al. A cell-penetrating peptidic GRP78 ligand for tumor cell-specific prodrug therapy. Bioorg Med Chem Lett. 2008 Mar 1;18(5):1632-6. DOI:10.1016/j.bmcl.2008.01.060
[3] Dorywalska M, et al. Effect of attachment site on stability of cleavable antibody drug conjugates. Bioconjug Chem. 2015 Apr 15;26(4):650-9. DOI:10.1021/bc5005747

FMoc-Val-Cit-PAB-PNP Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from FMoc-Val-Cit-PAB-PNP manufacturers

Qingdao RENAS Polymer Material Co., Ltd.

Product: (4-[(2S)-5-(carbamoylamino)-2-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylbutanamido]pentanamido]phenyl)methyl 4-nitrophenyl carbonate 863971-53-3
Price: US $0.00/kg
Min. Order: 20kg
Purity: 99%
Supply Ability: 20 tons
Release date: 2025-04-16

Xian confluore Biological Technology Co., Ltd.

Product: Fmoc-Val-Cit-PAB-PNP 863971-53-3
Price: US $0.00/g
Min. Order: 5g
Purity: >95.00%
Supply Ability: 5g
Release date: 2024-03-29

Career Henan Chemical Co

Product: FMoc-Val-Cit-PAB-PNP 863971-53-3
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100kg
Release date: 2020-02-18

863971-53-3, FMoc-Val-Cit-PAB-PNPRelated Search:

Fmoc-PEG5-NHS ester Fmoc-N-amido-PEG1-acid Fmoc-NH-PEG6-CH2COOH FMOC-12-AMINO-4,7,10-TRIOXADODECANOIC ACID FMOC-21-AMINO-4,7,10,13,16,19-HEXAOXAHENEICOSANOIC ACID Fmoc-PEG4-NHS ester Val-cit-PAB-OH pyrene-2,7-diyldiboronic acid Fmoc-Val-Cit-OH FMoc-Val-Cit-PAB MC-Val-Cit-PAB

{4-[(2S)-5-(carbamoylamino)-2-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylbutanamido]pentanamido]phenyl}methyl 4-nitrophenyl carbonate

Moc-Val-Cit-PAB-PNP

4-[[(2S)-1-amino-5-(carbamoylamino)-1-oxopentan-2-yl]-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]phenyl]methyl (4-nitrophenyl) carbonate

Fmoc-Val-Cit-PAB-PNP, >95%

FMoc-Val-Cit-PAB-PNP

(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

L-Ornithinamide, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]-

FMOC-VAL-CIT-PAB-PNP (9-FLUORENYLMETHYLOXYCARBONYL-VALYL-CITRULLYL-(4-AMINOBENZYL)-(4-NITROPHENYL)CARBONATE)

863971-53-3 FMoc-Val-Cit-PAB-PNP 1g

Fmoc-Val-Cit-PABC-PNP

Fmoc-Val-Cit-PAB-PNP-OH

Fmoc-Val-Cit-PAB-PN

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl]-L-ornithinamide

863971-53-3

63971-53-3

C40H42N6O10

7668

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