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
More
Less

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
More
Less

Safety

HS Code 
2924.29.7790
More
Less

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.

More
Less

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
250mg
Price
$337.5
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
LIN0000331
Product name
FMOC-VAL-CIT-PAB-PNP
Purity
95.00%
Packaging
5MG
Price
$497.55
Updated
2021/12/16
Iris Biotech GmbH
Product number
ADC1000
Product name
Fmoc-Val-Cit-PAB-PNP
Packaging
100mg
Price
$168.75
Updated
2021/12/16
More
Less

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

More
Less

FMoc-Val-Cit-PAB-PNP Suppliers

Americas 1 China 212 Europe 1 India 5 Japan 1 United States 12 Global 232
Shenzhen Yuzhong Pharmaceutical Technology Co., Ltd.
Tel
13414494621
Fax
qq: 30307604
Email
chenchao02lzu@126.com
Country
China
ProdList
134
Advantage
58
Zhenjiang Renzhi Biotechnology Co., Ltd.
Tel
18260638806
Email
865612999@qq.com
Country
China
ProdList
67
Advantage
58
YJ Pharma
Tel
13962794339
Email
3686954964@qq.com
Country
China
ProdList
270
Advantage
58
Chemyouth Life Science（Suzhou）Co.,Ltd
Tel
13752065514
Email
jianwei@chemyouth.com
Country
China
ProdList
133
Advantage
58
Shanghai Topbiochem Technology Co., Ltd
Tel
021-58170097
Email
info@topbiochem.com
Country
China
ProdList
9510
Advantage
58
Shenzhen HwaGen Pharmaceutical Co.,Ltd
Tel
17722620669
Fax
0752-5319394
Email
liangcong.yi@rafflespt.com
Country
China
ProdList
279
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
Advantage
61
TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28387
Advantage
80
TCI Europe
Tel
320-37350700
Fax
+32 (0)37350701
Email
sales@tcieurope.eu
Country
Europe
ProdList
23671
Advantage
75
TCI AMERICA
Tel
800-4238616
Fax
+1-888-520-1075 / +1-503-283-1987
Email
sales@tciamerica.com
Country
Americas
ProdList
23653
Advantage
75
More
Less

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
  • Pharmaceutical
  • ADCs
  • ADC-Linker
  • ADC-Linkers