A peptide linker molecule
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Val-Cit-PAB-OH

Item No. 34818

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide
CAS Number
159857-79-1
Synonyms
  • Valine-Citrulline-p-Aminobenzylcarbamate
  • VC-PAB
Molecular Formula
C18H29N5O4
Formula Weight
379.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
246 nm
SMILES
CC(C)[C@H](N)C(N[C@@H](CCCNC(N)=O)C(NC1=CC=C(C=C1)CO)=O)=O
InChi Code
InChI=1S/C18H29N5O4/c1-11(2)15(19)17(26)23-14(4-3-9-21-18(20)27)16(25)22-13-7-5-12(10-24)6-8-13/h5-8,11,14-15,24H,3-4,9-10,19H2,1-2H3,(H,22,25)(H,23,26)(H3,20,21,27)/t14-,15-/m0/s1
InChi Key
VEGGTWZUZGZKHY-GJZGRUSLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $134

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    50 mg

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    100 mg

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    250 mg

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    Cayman Chemical
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    Product Description

    Val-Cit-PAB-OH is a peptide linker molecule used in the synthesis of drug conjugates.1,2,3,4 It is cleaved by cathepsin B, a protease highly expressed in cancer cells, which confers specificity of the drug conjugates to cancer cells.1 Val-Cit-PAB-OH has been used in the synthesis of antibody-drug conjugates (ADCs) containing the tubulin polymerization inhibitors KGP05 or monomethyl auristatin D (MMAD), as well as α-galactosylceramide or folic acid conjugates that target peptide antigens to natural killer T cells or exportin 1 (CRM1) inhibitors to cancer cells, respectively.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dubowchik, G.M., Firestone, R.A., Padilla, L., 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. 13(4), 855-869 (2002).

    2. Dorywalksa, M., Strop, P., Melton-Witt, J.A., et al. Effect of attachment site on stability of cleavable antibody drug conjugates. Bioconjug. Chem. 26(4), 650-659 (2015).

    3. Anderson, R.J., Li, J., Kedzierski, L., et al. Augmenting influenza-specific T cell memory generation with a natural killer T cell-dependent glycolipid-peptide vaccine. ACS Chem. Biol. 12(11), 2898-2905 (2017).

    4. Klahn, P., Fetz, V., Ritter, A., et al. The nuclear export inhibitor aminoratjadone is a potent effector in extracellular-targeted drug conjugates. Chem. Sci. 10(20), 5197-5210 (2019).