ChemicalBook > CAS DataBase List > Val-cit-PAB-OH

Val-cit-PAB-OH

Product Name
Val-cit-PAB-OH
CAS No.
159857-79-1
Chemical Name
Val-cit-PAB-OH
Synonyms
H-Val-Cit-PAB-OH;(S)-2-((S)-2-amino-3-methylbutanamido)-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide;EOS-61316;al-Cit-PAB-OH;H-Val-Cit-PAB;H-Va1-Cit-PAB;Val-cit-PAB-OH;(D)-VAL-CIT-PAB;NH2-Val-Cit-PAB;ADC linker/ VAL-CIT-PAB
CBNumber
CB92715206
Molecular Formula
C18H29N5O4
Formula Weight
379.45
MOL File
159857-79-1.mol
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Val-cit-PAB-OH Property

Melting point:
168 °C(dec.)
Boiling point:
715.0±60.0 °C(Predicted)
Density 
1.243±0.06 g/cm3(Predicted)
storage temp. 
2-8°C(protect from light)
solubility 
DMF: 10 mg/ml; DMSO: 10 mg/ml; PBS (pH 7.2): 1 mg/ml
form 
powder to crystal
pka
13.75±0.46(Predicted)
color 
White to Almost white
InChIKey
VEGGTWZUZGZKHY-GJZGRUSLSA-N
SMILES
[C@H](CCCNC(=O)N)(C(=O)NC1C=CC(=CC=1)CO)NC(=O)[C@@H](N)C(C)C
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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

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
934356
Product name
Val-cit-PAB-OH
Purity
≥95%
Packaging
50MG
Price
$68.71
Updated
2025/07/31
Sigma-Aldrich
Product number
934356
Product name
Val-cit-PAB-OH
Purity
≥95%
Packaging
100MG
Price
$137.05
Updated
2025/07/31
TCI Chemical
Product number
V0155
Product name
Val-Cit-PAB-OH
Packaging
25MG
Price
$160
Updated
2025/07/31
TCI Chemical
Product number
V0155
Product name
Val-Cit-PAB-OH
Packaging
100MG
Price
$482
Updated
2025/07/31
TRC
Product number
V091545
Product name
Val-cit-PAB-OH
Packaging
100mg
Price
$580
Updated
2021/12/16
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Val-cit-PAB-OH Chemical Properties,Usage,Production

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.

Synthesis

159858-22-7

159857-79-1

The general procedure for synthesizing compound (CAS:159858-22-7) from compound (CAS:159857-79-1) is as follows: first, Fmoc-val-cit-PAB-OH (14.61 g, 24.3 mmol, 1.0 equiv; see U.S. Patent No. 6,214,345 by Firestone et al. ) was diluted with DMF (120 mL, 0.2 M). Diethylamine (60 mL) was added to this solution. The progress of the reaction was monitored by HPLC to confirm that the reaction was completed within 2 hours. Subsequently, the reaction mixture was concentrated and the resulting residue was precipitated using ethyl acetate (~100mL) under sonication for 10 minutes. After addition of ether (200 mL), the precipitate was further sonicated for 5 minutes. The solution was allowed to stand for 30 minutes without stirring, then filtered and dried under high vacuum to give Val-cit-PAB-OH, which was used in the next step without further purification. Yield: 8.84 g (96%). Next, Val-cit-PAB-OH (8.0 g, 21 mmol) was diluted with DMF (110 mL) and the resulting solution was treated with MC-OSu (6.5 g, 21 mmol, 1.0 eq.; see Willner et al. 1993, Bioconjugate Chem. 4: 521). After 2 hours of reaction, the completion of the reaction was confirmed on the basis of HPLC. The reaction mixture was concentrated and the resulting oil was precipitated with ethyl acetate (50 mL). After sonication for 15 minutes, ether (400 mL) was added and the mixture was further sonicated until all large particles were broken. The solution was then filtered and the solid dried to give an off-white solid intermediate. Yield: 11.63 g (96%); ES-MS m/z 757.9 [M-H].

IC 50

Protease Cleavable Linker; Cleavable Linker

References

[1] Patent: WO2007/8603, 2007, A1. Location in patent: Page/Page column 137; 165; 166
[2] Patent: WO2007/8848, 2007, A2. Location in patent: Page/Page column 108; 136; 137
[3] Patent: EP2486933, 2015, B1. Location in patent: Paragraph 0495
[4] Patent: WO2017/66668, 2017, A1. Location in patent: Paragraph 000190-000192
[5] Patent: CN107789630, 2018, A. Location in patent: Paragraph 0076; 0077; 0078

Val-cit-PAB-OH Preparation Products And Raw materials

Raw materials

Preparation Products

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Val-cit-PAB-OH Suppliers

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View Lastest Price from Val-cit-PAB-OH manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
Val-cit-PAB-OH 159857-79-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1Ton
Release date
2022-10-13
Xian confluore Biological Technology Co., Ltd.
Product
Val-Cit-PAB-OH 159857-79-1
Price
US $0.00/g
Min. Order
5g
Purity
>95.00%
Supply Ability
5g
Release date
2024-03-29
Career Henan Chemical Co
Product
Val-cit-PAB-OH 159857-79-1
Price
US $1.00/g
Min. Order
1g
Purity
≥98%
Supply Ability
g/kg/Ton
Release date
2020-03-05

159857-79-1, Val-cit-PAB-OHRelated Search:

Peptide T A20FMDV2 Peptide synthesis Peptide impurity peptide CRO OGP (Ostegenic Growth Peptide) Peptide phosphorylation marker Peptide fluorescent modification GMP peptide CMO FMoc-Val-Cit-PAB-PNP pyrene-2,7-diyldiboronic acid Fmoc-Val-Cit-OH FMoc-Val-Cit-PAB MC-Val-Cit-PAB

  • (S)-2-((R)-2-amino-3-methylbutanamido)-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide
  • EOS-61316
  • (S)-2-((S)-2-amino-3-methylbutanamido)-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide
  • L-Ornithinamide, L-valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-
  • Val-cit-PAB-OH
  • L-Valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide
  • NH2-Val-Cit-PAB
  • (D)-VAL-CIT-PAB
  • al-Cit-PAB-OH
  • H-Val-Cit-PAB-OH
  • 2-(4-(((2,6-dimethylbenzoyl)oxy)methyl)phenyl)aceticacid
  • H-Val-Cit-PAB
  • (2S)-2-[[(2S)-2-amino-3-methyl-butanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureido-pentanamide
  • H-Va1-Cit-PAB
  • ADC linker/ VAL-CIT-PAB
  • (S)-2-((S)-2-amino-N-(4-(hydroxymethyl)phenyl)-3-methylbutanamido)-5-ureidopentanamide
  • 159857-79-1
  • Linker
  • ADC LINKER
  • ADCs
  • ADC-Linkers